Reaction #814837

ord-aac61d426ebd406eaea7aa2c717b9d49

Reaction equation

COc1ccc(CS[C@H]2C[C@@H](C(=O)O)N(C(=O)OCc3ccc([N+](=O)[O-])cc3)C2)cc1
(2S,4S)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)-2-pyrrolidinecarboxylic acid
OCC1CNCCN1
2-hydroxymethylpiperazine
→
COc1ccc(CS[C@H]2C[C@@H](C(=O)N3CCNC(CO)C3)N(C(=O)OCc3ccc([N+](=O)[O-])cc3)C2)cc1
title compound
Yield 56.6%
COc1ccc(CS[C@H]2C[C@@H](C(=O)N3CCNC(CO)C3)N(C(=O)OCc3ccc([N+](=O)[O-])cc3)C2)cc1
(2S,4S)-2-(3-Hydroxymethyl-1-piperazinylcarbonyl)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine
Yield 56.6%

Reactants

COc1ccc(CS[C@H]2C[C@@H](C(=O)O)N(C(=O)OCc3ccc([N+](=O)[O-])cc3)C2)cc1
(2S,4S)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)-2-pyrrolidinecarboxylic acid
—
N,N'-carbonyldiimidazole
OCC1CNCCN1
2-hydroxymethylpiperazine

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherthat described in Preparation 8

Procedure

Following a procedure similar to that described in Preparation 8, but using 10.0 g of (2S,4S)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)-2-pyrrolidinecarboxylic acid, 4.4 g of N,N'-carbonyldiimidazole and 4.0 g of 2-hydroxymethylpiperazine, 6.9 g of the title compound were obtained, as a powder.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05712267uspto-grants-1998_01