tert-Butyl N-[2-(N-isobutyl-4-meth­oxy­benzene­sulfonamido)­eth­yl]carbamate

Xiao-Guang Bai; Ju-Xian Wang

doi:10.1107/S1600536814009143

. 2014 May 17;70(Pt 6):o674. doi: 10.1107/S1600536814009143

tert-Butyl N-[2-(N-isobutyl-4-methoxybenzenesulfonamido)ethyl]carbamate

Xiao-Guang Bai ^a, Ju-Xian Wang ^a,^*

PMCID: PMC4051064 PMID: 24940254

Abstract

The title compound, C₁₈H₃₀N₂O₅S, was synthesized by the reaction of tert-butyl 2-(isobutylamino)ethylcarbamate with p-methoxyphenylsulfonyl chloride. In the molecule, two intramolecular C—H⋯O hydrogen bonds are observed. In the crystal, molecules are linked by N—H⋯O hydrogen bonds involving the imino group N atom and the ester group O atom into chains running parallel to the b axis. The chains are further connected by C—H⋯O hydrogen bonds, forming layers parallel to the bc plane.

Related literature

For potential HIV-1 protease inhibitors, see: Surleraux et al. (2005 ▶); Ghosh et al. (2006 ▶, 2011 ▶); Guo et al. (2010 ▶). For the structure of the methoxy analogue, see: Chatziefthimiou et al. (2006 ▶)

Experimental

Crystal data

C₁₈H₃₀N₂O₅S
M _r = 386.50
Monoclinic,
a = 19.2484 (5) Å
b = 5.29088 (12) Å
c = 20.1825 (6) Å
β = 92.497 (3)°
V = 2053.46 (9) Å³
Z = 4
Cu Kα radiation
μ = 1.65 mm⁻¹
T = 293 K
0.28 × 0.16 × 0.14 mm

Data collection

Agilent Xcalibur (Atlas, Gemini ultra) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013 ▶) T _min = 0.776, T _max = 1.000
11865 measured reflections
3658 independent reflections
3122 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.089
S = 1.05
3658 reflections
245 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2013 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL/PC.

Supplementary Material

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814009143/rz5120sup1.cif

e-70-0o674-sup1.cif^{(21.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814009143/rz5120Isup2.hkl

e-70-0o674-Isup2.hkl^{(179.4KB, hkl)}

Click here for additional data file.^{(7.1KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814009143/rz5120Isup3.cml

CCDC reference: 998938

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O2	0.97	2.43	2.9106 (19)	110
C13—H13A⋯O3	0.97	2.48	3.107 (2)	122
C3—H3⋯O4ⁱ	0.93	2.59	3.402 (2)	147
N2—H2A⋯O4ⁱⁱ	0.82 (2)	2.38 (2)	3.190 (2)	171 (2)

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

Acknowledgments

We are grateful for the financial support from the National Natural Science Foundation of China (No. 81302644).

supplementary crystallographic information

1. Comment

As a part of our ongoing project aimed at the development of potential HIV-1 protease inhibitors (Surleraux et al., 2005; Ghosh et al., 2006, 2011; Guo et al., 2010), we have synthesized the title compound and report its crystal structure herein.

The molecular structure of the title compound is illustrated in Fig. 1. Bond distances and angles are similar to those found in the methoxy analogue (Chatziefthimiou et al., 2006). The molecular conformation is stabilized by two intramolecular C—H···O hydrogen bonds (Table 1). In the crystal, the molecules are linked into chains by intermolecular N—H···O hydrogen bonds (Table 1) parallel to the b axis (Fig. 2), which are further connected to form layers parallel to the bc plane by C—H···O hydrogen bonds (Table 1).

2. Experimental

To a solution of tert-butyl 2-(isobutylamino)ethylcarbamate (1.13 g, 5.2 mmol) and "N,N-diisopropylethylamine (1.34 g, 10.4 mmol) in dichloromethane (10 ml) was added dropwise a solution of p-methoxyphenylsulfonyl chloride (1.18 g, 5.7 mmol) in dichloromethane (3 ml) over a period of 10 min at room temperature. The reaction mixture was stirred for 5 h at the same temperature and concentrated under reduced pressure. tert-Butyl 2-(N-isobutyl-4-methoxyphenylsulfonamido)ethylcarbamate was obtained as a white solid by flash chromatography (40 g silica gel, petroleum ether/AcOEt, 1:10 v/v). The yield is 42%. Colourless block crystals suitable for X-ray diffraction were obtained in 3 day by slow evaporation of a petroleum ether/AcOEt (4:1 v/v) solution.