2,5-Dioxopyrrolidin-1-yl 3-(furan-2-yl)acrylate

Haifeng Zhu; Miao Guo; Han Chen; Haixiao Jin; Hongze Liang

doi:10.1107/S1600536811040566

. 2011 Oct 8;67(Pt 11):o2863. doi: 10.1107/S1600536811040566

2,5-Dioxopyrrolidin-1-yl 3-(furan-2-yl)acrylate

Haifeng Zhu ^a, Miao Guo ^a, Han Chen ^a, Haixiao Jin ^a, Hongze Liang ^a,^*

PMCID: PMC3247598 PMID: 22219903

Abstract

The title compound, C₁₁H₉NO₅, was prepared by the reaction of 2-furanacrylic acid and N-hydroxysuccinimide. The molecule consists of two approximately planar moieties, viz. a succinimide group and the rest of the molecule [the largest deviations from the least-squares planes are 0.120 (1) and 0.210 (1) Å, respectively]. The dihedral angle between these fragments is 63.70 (5)°. In the crystal, molecules are linked by C—H⋯O hydrogen bonds into two-dimensional nets.

Related literature

For derivatives of N-hydroxysuccinimide, see: Anderson et al. (1964 ▶); Blumberg & Vallee (1975 ▶); Brown et al. (2005 ▶); Cheng et al. (2007 ▶); Jones (2003 ▶).

Experimental

Crystal data

C₁₁H₉NO₅
M _r = 235.19
Orthorhombic,
a = 10.3054 (13) Å
b = 9.2376 (12) Å
c = 21.892 (3) Å
V = 2084.0 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 296 K
0.30 × 0.30 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.977, T _max = 0.977
16939 measured reflections
2399 independent reflections
1900 reflections with I > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.082
S = 1.02
2399 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811040566/yk2020sup1.cif

e-67-o2863-sup1.cif^{(15.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811040566/yk2020Isup2.hkl

e-67-o2863-Isup2.hkl^{(118KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811040566/yk2020Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯O1ⁱ	0.93	2.48	3.3533 (17)	156
C14—H14A⋯O5ⁱⁱ	0.93	2.45	3.3672 (18)	169

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

This project was supported by Zhejiang Provincial Natural Science Foundation of China (grant No. Y4100113), the National Natural Science Foundation of China (grant No. 20903058), the Natural Science Foundation of Ningbo City (grant Nos. 2009 A610047, 2010 A610025, 2010 A610027) and the K. C. Wong Magna Fund of Ningbo University.

supplementary crystallographic information

Comment

N-Hydroxysuccinimide is frequently used in organic chemistry as an activating reagent, which readily form crystalline adducts with amines or acids (Jones, 2003). N-Hydroxysuccinimide esters are widely used as leaving groups to activate carboxylic acids (Cheng et al., 2007). The title compound N-(2-furanacryloyl)-succinimide ester is an intermediate of FAPGG which is the substrate of diagnostic reagent. We have used a simple procedure to synthesize the title compound in reasonable yields (Blumberg & Vallee, 1975; Brown et al., 2005).

The molecular structure of the title compound (I) is shown in Fig.1. In the molecule, the dihedral angle between the furan and succinimide rings is 56.26 (43)°. In the crystal structure, molecules are linked by the C12—H12···O1ⁱ hydrogen bonds to form chains along a and C14—H14···O5ⁱⁱ hydrogen bonds to form chains along b directions.

Experimental

2-Furanacrylic acid (13.81 g, 0.10 mol), N-hydroxysuccinimide (11.51 g, 0.10 mol) and dicyclohexylcarbodiimide (20.63 g, 0.10 mol) were added to 200 ml dioxane in a round flask. This mixture was stirred at 4°C for 14 h before the dicyclohexylurea was removed by filtration. Then the resulting dark brown filtrate was evaporated in vacuum to give the dark brown residue. Slight brown crystals were obtained by recrystallization from 2-propanol (15.29 g, 65%). 1H NMR(400 MHz, CDCl3): \d 7.62 (d, J=16 Hz, 1H), 7.56 (d, J=1.6 Hz, 1H), 6.77 (d, J=3.6 Hz, 1H), 6.53–6.52 (dd, J=3.6 Hz, J=1.6 Hz, 1H), 6.47 (d, J=16 Hz, 1H), 2.87 (s, 4H).