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. 2026 Feb 3;11(6):9381–9387. doi: 10.1021/acsomega.5c09302

Thionyl Chloride-Mediated One-Pot O‑, N‑, and S‑Deacetylation and Esterification of a Diverse Series of Acetoxy, Acetamido, and Thioacetate Carboxylic Acids

Tanvir Khaliq 1,*, Veerpal Kaur 1
PMCID: PMC12917795  PMID: 41726691

Abstract

Thionyl chloride (SOCl2) has been extensively used as a chlorinating reagent for the esterification of carboxylic acids via the formation of an acid chloride intermediate. While SOCl2-mediated deacetylation of acetoxy (O-deacetylation) and acetamido (N-deacetylation) esters is rare and has been reported on a coumarin substrate, deacetylation of thioacetate (S-deacetylation) esters by SOCl2 is unknown. Furthermore, a simultaneous deacetylation and esterification of acetoxy, acetamido, and thioacetate carboxylic acids in a one-pot synthetic scheme has not been reported in the literature. We report deacetylation and esterification of a diverse series of acetoxy carboxylic acids mediated by SOCl2, with examples from acetamido and thioacetate carboxylic acids to obtain hydroxy, amino, and thiol esters in a one-pot procedure. The reaction can be conveniently carried out at room temperature for 8–18 h, followed by an aqueous workup in good to excellent yields and has a very broad substrate scope.

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1. Introduction

Acetylation and deacetylation of alcohols, phenols, thiols, acids, and amines are useful synthetic protecting and deprotecting strategies to optimize the reaction conditions and yields, particularly in the total synthesis of medicinally important scaffolds. − Esterification of carboxylic acids is also an important protecting strategy to reduce the polarity of acidic functionality and enhance the organic solubility, reactivity, as well as the product yields. , The two synthetically important transformations have been accomplished separately to generate synthetically useful intermediates for pharmacologically and agrochemically active compounds. Thionyl chloride (SOCl2), PCl5, POCl3, and acetyl chloride have been extensively used to generate synthetically useful esters via acid chloride intermediates to enhance the solubility, leaving group capability, and purification of carboxylic acids. − Deacetylation of esters is employed in the late-stage synthesis of synthetically and pharmacologically useful compounds. A chemo-selective deacetylation of acetyl- and benzoyl-protected carbohydrates using aqueous HCl has recently been reported. However, thionyl chloride has not been frequently used for the deacetylation of esters. SOCl2-mediated deacetylation of acetoxy and acetamido coumarins to alcohols (1) and amines (2), respectively, have recently been reported on a single substrate (Scheme ). SOCl2 has also been used to deacetylate N-arylacetamides to aromatic amines (3).

1. (i–vi) Products (1–7) Obtained via O-, N-, and S-Deacetylation of Acylated Substrates (Previous Work); (vii) Product (8) Obtained via a Concurrent Deacetylation and Esterification of (R)-3-Acetoxy-o-amidosuccinanilic Acid in a One-Pot Scheme (Present Work). The Sites of Reactions are Highlighted in Bold.

1

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Acetyl chloride-mediated S-deacetylation of thioacetates to thiols (4) has been reported with a limited substrate scope. Furthermore, a chemoselective deacetylation of various esters has also been accomplished using a catalytic amount of acetyl chloride to furnish the corresponding alcohols (5). However, due to its lack of dual deacetylation and esterification, hydrolytic instability, nonversatility, and hazardous nature, acetyl chloride may have limited use in deacetylation and esterification. The S-deacetylation of a few thioacetates to thiols has been performed in situ using pyrrolidine. The O- and S-deacetylation of deoxyglycosides have also been accomplished in hydrolytic conditions in methanol to obtain the desired product (6). , A chemoselective O-deacetylation of functionalized esters has been carried out using dioxomolybdenum dichloride (MoO2Cl2) to afford the desired alcohol (7). However, due to long reaction times (27–290 h), limited substrate scope, cumbersome reaction setup, and air instability (can oxidize to molybdenum trioxide), this oxidometallic reagent may not be suitable for dual deacetylation and esterification. Recently, O-deacetylation has been performed using trimethylsulfonium iodide (Me3SI), KMnO4, and tetranuclear zinc cluster (Zn4(OCOCF3)6O) catalysis, whereas N-deacetylation of amino sugars has also been accomplished using triflic anhydride and 2-fluoropyridine. However, Me3SI methodology uses a highly toxic and corrosive oxidizing agent, KMnO4, as an additive, which is also inert to the deacetylation of the acetamido group and is light-sensitive. Both Me3SI and KMnO4 methods also lack the broad substrate specificity such as S- and N-deacetylation and the dual advantages of deacetylation and esterification shown by thionyl chloride. The key parameters of the SOCl2-mediated deacetylation method are compared with those previously reported as follows (Table ).

1. Comparison between SOCl2-Mediated Deacetylation and Reported Methods .

Reagent Temp. Catalyst loading Substrate type Functional gp. compatibility
AcCl rt 0.10–0.5 equiv aliphatic/aromatic/sugar BnO, TsO, PivO, BzO
MoO2Cl2 rt, reflux 0.05 equiv aliphatic/benzylic/sugar BnO, NHAc, NHBz, PivO
Me3SI/KMnO4 rt 0.1/0.1 equiv aliphatic/aromatic/sugar/steroid BzO, BnO, CO2Me, NHAc
KMnO4 rt 0.01–1.0 equiv aliphatic/aromatic/sugar/steroid NHAc, BnO, PivO, CO2Me
SOCl2 rt 1.6–10 equiv aliphatic/aromatic/benzylic/acrylic/S-acetyl/N-acetyl CONH2, OCH3
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a

BnO (benzyl), BzO (benzoyl), PivO (pivaloyl), TsO (tosyl), NHAc (N-acetyl), NHBz (N-benzyl), CO2Me (methyl ester), OCH3 (methoxy).

Thionyl chloride was also preferred to acidic hydrolysis or catalytic hydrolysis due to nonselectivity and harsh conditions such as conc. hydrochloric acid needed for the latter reactions. Unlike the above-reported deacetylation methods, our method has dual advantage of deacetylation and esterification, broad substrate specificity, gaseous side products giving rise to cleaner reaction, selectivity, ease of reaction, and use of a relatively less hazardous and stable reagent. SOCl2-mediated esterification is also a useful protection strategy in medicinal chemistry since it converts alcohols and carboxylic acids into reactive chloride derivatives, which are important intermediates for constructing biologically active natural products and their derivatives.

Thionyl chloride-mediated S-deacetylation of thioacetates is not known, and deacetylation and esterification of O-, S-, and N-acetylated carboxylic acids in a one-pot scheme have not been reported. We report the SOCl2-mediated deacetylation and esterification reaction of acetoxy, acetamido, and thioacetate carboxylic acids for the first time (Scheme ; vii). This reaction can be efficiently and conveniently carried out at room temperature using a simple aqueous workup. The deacetylated esters can be obtained in good to excellent yields and the reaction can be accomplished on a wide variety of substrates such as aliphatic, aromatic, acrylic, and sterically hindered acetoxy carboxylic acids.

2. Results and Discussion

We are designing and synthesizing novel analogs of the orally active antileishmanial lead natural product peganine , for evaluation against the neglected tropical parasitic diseases leishmaniasis, , and human African trypanosomiasis (African sleeping sickness) as well as cancer. While carrying out the total synthesis of the lead molecule, one of the steps involved the formation of a methyl ester of the 3-acetoxy succinic anthranilic acid substrate, 8a (Scheme ). We used thionyl chloride and methanol , for esterification of the substrate using anhydrous dichloromethane as solvent to generate the desired 3-acetoxy methyl ester. Dichloromethane was used due to its easy evaporation and compatibility with our workup. Upon variation of the reaction time, the reaction also afforded an unexpected 3-hydroxy methyl ester (8) with the loss of the acetyl group from C-3. Following the optimization of the number of equivalents for thionyl chloride and methanol and time, various phenyl-substituted 3-acetoxy succinic anthranilic acids were evaluated to probe the benzenoid ring for electronic effects.

2. (i) SOCl2, MeOH, Dichloromethane, rt, 18 h.

2

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The reaction (Scheme and Table ) of (R)-3-acetoxy-4-((2-carbamoylphenyl)­amino)-4-oxobutanoic acid (8a) with SOCl2 and methanol in dichloromethane led to esterification of C-1 carboxylic acid and deacetylation of the C-3 acetoxy group to yield the 3-hydroxy ester (8) in moderate yield (29%). The lower yield of compound 8 was primarily due to the formation of the side product, 3-acetoxy ester (25), which was confirmed by the negative molecular ion peak at m/z 307.0, 1H NMR, and 13C NMR spectroscopy (Figures S49–S51) as well as due to unreacted starting material. The effects of either electron-donating or electron-withdrawing groups on deacetylation and esterification were also assessed. The 3-acetoxy-o-amidosuccinanilic acid substrate (9a) containing the electron-donating methyl group afforded the desired product (9) in a lower yield (11%), whereas the substrates (10a and 11a) containing electron-withdrawing fluoro- and chloro- groups afforded the desired products (10 and 11) in comparatively better yields (55% and 39%). Because the proposed deacetylation most likely proceeds with the nucleophilic attack of methanol on the acetate carbonyl, electron-withdrawing groups at the para-positions of the nearby phenyl ring may further enhance the electrophilicity of the carbonyl, facilitating the formation of the tetrahedral intermediate.

2. Structures of Substrates, Reactions Conditions, and Isolated Product Yields.

2.

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a

The % yields are isolated as determined by column chromatography, and the table uses the same isolated % values as Supporting Information.

Next, with the reaction conditions optimized, we investigated the substrate scope of our methodology (Scheme and Table ). First, we used 6-acetoxy-2-naphthoic acid (12a) to assess its simultaneous deacetylation and esterification, but the yield of the desired product (12) was moderate (25%). However, when substrates such as 3-(4-acetoxy-3-methoxyphenyl) acrylic acid (14a) and the 3-acetoxy-2-methylbenzoic acid (15a) were subjected to our reaction conditions, the yield of the desired products (14 and 15) increased to 51% and 43%, respectively. The relatively lower yields of hydroxy esters 14 and 15 may be attributed to the steric hindrance of methoxy and methyl groups with acetoxy groups, resulting in reduced deacetylation. The unsubstituted 3-(2-acetoxyphenyl) acrylic acid (16a) afforded the corresponding methyl 3-(2-hydroxyphenyl) acrylic ester (16) in excellent yield (85%), suggesting that the absence of steric bulk around the acetate carbonyl facilitates the nucleophilic attack by methanol. Unlike in substrate 16a, the presence of an ortho-methoxy group to the acetate moiety in 14a leads to steric hindrance to the nucleophilic attack by methanol on the acetate carbonyl, thereby reducing the formation of deacetylated ester 14. This was further corroborated with optimization of 14, which resulted in a lower yield (68%) than 16 (85%), albeit higher than obtained before optimization (51%). The detailed yield optimization of 14 is shown in Table S1. Upon varying the molar ratios of thionyl chloride, moderate loading (1.6 and 3.2 equiv) led to improved yield (68% and 63%) as compared to higher loading (5 equiv) in which the yield was 51% in 16 h. Also, a higher reaction time (24 h) led to a lower yield (47%) of 14 as compared to a lower reaction time (16 h). However, 5 equiv of SOCl2 were optimum for S-acetyl, N-acetyl, and benzylic substrates.

3. (i–iv) SOCl2, MeOH, Dichloromethane, rt, 16 h.

3

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We also evaluated simple benzoic acids such as 4-acetoxybenzoic acid (17a) and 2-acetoxybenzoic acid (aspirin), 18a. The reactions (Scheme and Table ) afforded the desired products (17 and 18) in lower yields (11% and 2%). The low yield in aspirin may be due to the intramolecular hydrogen bonding and/or steric hindrance of the acetoxy moiety with ortho-carboxyl, as exemplified by the lower yield for 14 (68%) compared to 16 (85%). We repeated the reaction for aspirin by refluxing and extending the reaction time, but the yields of product 18 were consistently lower. However, when we tested 2-acetoxy-2-phenylacetic acid (19a), the desired product (19) was obtained in a higher yield (72%).

4. (i) SOCl2, MeOH, DCM, rt, 16 h; (ii) SOCl2, MeOH, DCM, Reflux, 12 h; (iii) SOCl2, MeOH, DCM, rt, 12 h.

4

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3. Structures of Substrates, Reactions Conditions, and Isolated Product Yields.

2.

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a

The % yields are isolated as determined by column chromatography and the table uses the same isolated % values as Supporting Information.

b

Reflux temperature is 40 °C.

To further broaden the scope of our synthetic methodology, we extended O-deacetylation and methyl esterification to S-deacetylation and N-deacetylation and ethyl esterification (Scheme and Table ). The S-deacetylation and esterification of 2-S-acetyl acetic acid (20a) afforded the desired thiol ester (20) in excellent yield (77%), whereas the N-deacetylation and esterification of 4-acetamido benzoic acid (21a) yielded the desired amine (21) in a very high yield (84%). This shows that our methodology can be successfully applied to S- and N-deacetylation reactions.

5. (i) SOCl2, MeOH, DCM, rt, 8 h; (ii) SOCl2, MeOH, DCM, rt, 16 h; (iii, and iv) SOCl2, EtOH, DCM, rt, 16 h.

5

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Finally, we diversified our methodology to include esterification of carboxylic acid using ethanol (Scheme and Table ). The O-deacetylation and esterification of 3-(4-acetoxy-3-methoxyphenyl) acrylic acid (14a) using SOCl2 and ethanol afforded the desired phenol (22) in low yield (12%). However, the O-deacetylation and esterification of 3-acetoxy-2-methyl benzoic acid (15a) generated the desired product (23) in a higher yield (36%). The lower yields of both products may be due to the lower reactivity of ethanol as compared to methanol. It appears that this synthetic extension of our methodology is not significant. Nevertheless, our methodology can be successfully applied to all three commonly encountered O-, N-, and S-deacetylation as well as methyl and ethyl esterification reactions of acetoxy, acetamido, and thioacetate carboxylic acids to obtain synthetically useful alcohol, amine, and thiol esters, respectively.

A proposed mechanism of SOCl2-mediated deacetylation and esterification is depicted as follows (Scheme ) and is based on the analogy with the known SOCl2 chemistry. The reaction may be initiated by a nucleophilic attack of the hydroxyl group of (R)-3-acetoxy-o-amidosuccinanilic acid (A) on the sulfoxide moiety to form a chlorosulfite intermediate (B). The loss of SO2 and HCl from the intermediate (B) with a simultaneous protonation of its acetoxy group may lead to nucleophilic attack by methanol to generate a highly unstable tetrahedral intermediate (C). The stabilization of the intermediate due to the loss of methyl acetate may occur concurrently with another nucleophilic attack by methanol on the acetyl chloride moiety in C, followed by deprotonation, resulting in the formation of the target compound, methyl (R)-3-hydroxy-o-amidosuccinianilate (D). Additional control experiments using deuterated methanol or running the reaction without methanol are needed in future studies to confirm the mechanism of deacetylation and esterification.

6. Proposed Mechanism (i) Formation of Chlorosulfite Intermediate (B), (ii) Formation of Tetrahedral Intermediate (C), and (iii) Formation of Methyl (R)-3- Hydroxy-o-amidosuccinanilate (D).

6

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2.1. Application in Natural Product Synthesis

We successfully employed the deacetylated ester intermediates (8–11) for the synthesis of our tetrahydropyrroloquinazoline alkaloid natural products and their analogs for the protozoan parasitic disease leishmaniasis. Compound 8 was subjected to LAH-mediated reduction (Scheme ) to obtain the biologically active natural product, (R)-3-hydroxypegamine (24) in excellent yield (70%). The reaction involves a chemo-selective reduction of ester 8, which upon aqueous workup, undergoes in situ LiOH-catalyzed dehydrative ring closure to yield 3-hydroxypegamine (Figures S46–S48). Mhaske and Argade have synthesized the S-isomer of 24 using highly unstable diazomethane as the methylating agent with 2 equiv of LAH. Our method has an advantage of using a safer alternative in thionyl chloride with only 1 equiv of LAH to accomplish the synthesis of hydroxypegamine. This clearly demonstrates the application of our methodology in the synthesis of biologically active natural products.

7. Lithium Aluminum Hydride, THF, 0–5 °C (10 min), rt (1 h), Aqueous Workup and THF (2 h).

7

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2.2. Scope Limitation

We observed a scope limitation of our synthetic methodology. The bioisosteric replacement (Scheme and Table ) of a benzenoid ring with the heterocyclic pyridine in 3-acetoxypyridosuccinanilic acid (26a) failed as it did not yield the desired 3-hydroxy ester (26). Analysis of ESI-MS of the reaction mixture showed 3-acetoxy ester (methyl (R)-3-acetoxy-4-((3-carbamoylpyridin-2-yl)­amino)-4-oxobutanoate) at m/z 310.1 [M + H]+ as the principal side product formed during the reaction (Figure S52).

8. (i) SOCl2, MeOH, Dichloromethane, rt, 16 h.

8

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3. Conclusion

In conclusion, we have developed an efficient one-pot O-, N-, and S-deacetylation and esterification of a diverse set of acetoxy, acetamido, and thioacetate carboxylic acids mediated by thionyl chloride and methanol or ethanol in dichloromethane at room temperature. The methodology can be successfully applied to various aliphatic, aromatic, and cinnamic acids, as well as to sterically hindered substrates such as mandelic acid, to obtain synthetically useful building blocks in good to excellent yields and has a very broad substrate scope. The succinanilate intermediates are frequently employed in the synthesis of biologically active quinazoline alkaloid natural products and their analogs. Our laboratory is using derivatives of methyl 3-hydroxy succinanilate esters for the synthesis of the antileishmanial lead compounds and their analogs.

Supplementary Material

ao5c09302_si_001.pdf (3.9MB, pdf)

Acknowledgments

We greatly acknowledge the funding support from the SDSU Haarberg 3D (Drug, Disease, and Delivery) Research Center, SDSU Research and Scholarly and Creative Activity (RSCA) grant, and the South Dakota Board of Regents Competitive Research Grant (CRG). We thank the SDSU Core NMR Laboratory for the acquisition of the NMR data of our compounds. The HRMS data were acquired using the resources of the Chemistry Instrument Center (CIC), University at Buffalo, SUNY, Buffalo, NY, che-ic@buffalo.edu. We greatly appreciate the hard work and dedication of our two PharmD students, Hyunjun (June) Cho and Lainee Mentzer, for helping synthesize the fluoro- and chlorosuccinanilate derivatives, respectively. Master’s student, Sunitha Jada is acknowledged for her efforts on the pyridyl substrate.

The data underlying this study are available in the published article and its Supporting Information.

The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acsomega.5c09302.

  • General experimental details, synthetic procedures, spectroscopic characterization, HRMS, 1H NMR, and 13C NMR of compounds 8–26, and yield optimization of 14 (PDF)

The authors declare no competing financial interest.

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

ao5c09302_si_001.pdf (3.9MB, pdf)

Data Availability Statement

The data underlying this study are available in the published article and its Supporting Information.

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