Reaktion #814836

ord-d2f835f5eaf84ef1a4382d923d62a93f

Reaktionsgleichung

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
CC(C)(C)C(=O)Cl
pivaloyl chloride
O=C(N[C@@H]1CCNC1)OCc1ccc([N+](=O)[O-])cc1.O=C(O)C(F)(F)F
(3R)-3-(4-nitrobenzyloxycarbonyl)aminopyrrolidine trifluoroacetate
→
O=C(N[C@@H]1CCN(C(=O)[C@@H]2C[C@H](S)CN2C(=O)OCc2ccc([N+](=O)[O-])cc2)C1)OCc1ccc([N+](=O)[O-])cc1
title compound
Ausbeute 65.8%
O=C(N[C@@H]1CCN(C(=O)[C@@H]2C[C@H](S)CN2C(=O)OCc2ccc([N+](=O)[O-])cc2)C1)OCc1ccc([N+](=O)[O-])cc1
(2S,4S)-4-Mercapto-2-[(3R)-3-(4-nitrobenzyloxycarbonyl)aminopyrrolidin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine
Ausbeute 65.8%

Edukte

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
CC(C)(C)C(=O)Cl
pivaloyl chloride
O=C(N[C@@H]1CCNC1)OCc1ccc([N+](=O)[O-])cc1.O=C(O)C(F)(F)F
(3R)-3-(4-nitrobenzyloxycarbonyl)aminopyrrolidine trifluoroacetate

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigethat described in Preparation 18

Vorschrift

Following a procedure similar to that described in Preparation 18, but using 1.29 g of (2S,4S)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)-2-pyrrolidinecarboxylic acid, 365 mg of pivaloyl chloride and 1.14 g of (3R)-3-(4-nitrobenzyloxycarbonyl)aminopyrrolidine trifluoroacetate, 1.09 g of the title compound were obtained as a powder.

Quelle

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