2-Nitrobenzenesulfonyl chloride → n-[2-(2-Nitro-benzenesulfonylamino)-ethyl]-alanine ethyl ester

HRID 1794935Notes

Reaction equation

HRID 1794935 reaction equation
Cl.Cl.[CH2:3]([O:5][C:6](=[O:13])[C@H:7]([CH3:12])[NH:8][CH2:9][CH2:10][NH2:11])[CH3:4].[N+:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23](Cl)(=[O:25])=[O:24])([O-:16])=[O:15]>>[CH2:3]([O:5][C:6](=[O:13])[C@H:7]([CH3:12])[NH:8][CH2:9][CH2:10][NH:11][S:23]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[N+:14]([O-:16])=[O:15])(=[O:24])=[O:25])[CH3:4]

Participants

3

Reactant 2

HCID 155402-Nitrobenzenesulfonyl chlorideHCID 23404547N-(2-Aminoethyl)-alanine ethylester 2HCl

Product 1

HCID 69667099n-[2-(2-Nitro-benzenesulfonylamino)-ethyl]-alanine ethyl esterYield 95%

Procedure

N-(2-Aminoethyl)-alanine ethyl ester 2HCl (1.165 g, 5.0 mmol), prepared as described by Puschl (A. Puschl et al., Tetrahedron, 1998, 39, 4707–4710.), was reacted with 2-nitro-benzenesulfonyl chloride (1.11 g 5.0 mmol) as per the procedure of example 13 to give the title compound (1.64 g, 95%). 1H-NMR (500 MHz; DMSO-d6) δ 8.02˜7.96 (m, 2H), 7.86 (m, 2H), 4.05 (q, 2H), 3.16 (q, 1H), 2.94 (t, 2H), 2.58 (m, 1H), 2.43 (m, 1H), 1.17 (t, 3H), 1.09 (d, 3H).

Sources & evidence

ORD record
ord-7df3e6032e0642e4bb82548fcf261f44
Source dataset
uspto-grants-2006_04
Patent number
US07022851B2

Reaction notes

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