Reaktion #449234

ord-124d1006aa94472386b7e5e7683f6003

Reaktionsgleichung

COc1ccc(CS[C@H]2C[C@@H](C(=O)O)N(C)C2)cc1
(2S,4S)-4-(4-methoxybenzylthio)-1-methyl-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
(3S)-3-(4-nitrobenzyloxycarbonyl)aminopyrrolidine trifluoroacetate
→
CN1C[C@@H](S)C[C@H]1C(=O)N1CC[C@H](NC(=O)OCc2ccc([N+](=O)[O-])cc2)C1
title compound
Ausbeute 71.6%
CN1C[C@@H](S)C[C@H]1C(=O)N1CC[C@H](NC(=O)OCc2ccc([N+](=O)[O-])cc2)C1
(2S,4S)-4-Mercapto-2-[(3S)-3-(4-nitrobenzyloxycarbonyl)aminopyrrolidin-1-ylcarbonyl]-1-methylpyrrolidine
Ausbeute 71.6%

Edukte

COc1ccc(CS[C@H]2C[C@@H](C(=O)O)N(C)C2)cc1
(2S,4S)-4-(4-methoxybenzylthio)-1-methyl-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
(3S)-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 1.03 g of (2S,4S)-4-(4-methoxybenzylthio)-1-methyl-2-pyrrolidinecarboxylic acid, 463 mg of pivaloyl chloride and 1.45 g of (3S)-3-(4-nitrobenzyloxycarbonyl)aminopyrrolidine trifluoroacetate, 1.07 g of the title compound were obtained as a powder.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05866564uspto-grants-1999_02