Reaktion #10041

ord-e90368ffd2234df394e85e5cab1a5b4f

Reaktionsgleichung

CC(C)(C)OC(=O)N1CC[C@H](NC(=O)CNC(=N)NC(=O)OCc2ccc([N+](=O)[O-])cc2)C1
(S)-1-(t-butyloxycarbonyl)-3-[2-[3-(4-nitrobenzyloxycarbonyl)guanidino]acetylamino]pyrrolidine
O=S(=O)(O)O
sulfuric acid
CC(C)OC(C)C
Diisopropyl ether
→
N=C(NCC(=O)N[C@H]1CCNC1)NC(=O)OCc1ccc([N+](=O)[O-])cc1.O=S(=O)(O)OS(=O)(=O)O
title compound
Ausbeute 95.4%
N=C(NCC(=O)N[C@H]1CCNC1)NC(=O)OCc1ccc([N+](=O)[O-])cc1.O=S(=O)(O)OS(=O)(=O)O
(S)-3-[2-[3-(4-nitrobenzyloxycarbonyl)guanidino]acetylamino]pyrrolidine disulfate
Ausbeute 95.4%

Edukte

CC(C)(C)OC(=O)N1CC[C@H](NC(=O)CNC(=N)NC(=O)OCc2ccc([N+](=O)[O-])cc2)C1
(S)-1-(t-butyloxycarbonyl)-3-[2-[3-(4-nitrobenzyloxycarbonyl)guanidino]acetylamino]pyrrolidine
O=S(=O)(O)O
sulfuric acid
CC(C)OC(C)C
Diisopropyl ether

Reagenzien

Keine

Lösungsmittel

CO
methanol

Reaktionsbedingungen

Temperatur
42.5°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturThe reaction mixture was cooled to from 20 to 30° C.
  2. 2
    workup.STIRRINGwas stirred at the same temperature for 0.5 hours
  3. 3
    workup.STIRRINGwas stirred at the same temperature for 1 hour
  4. 4
    SonstigeThe crystals which precipitated
  5. 5
    Filtrationwere collected by filtration

Vorschrift

(S)-1-(t-butyloxycarbonyl)-3-[2-[3-(4-nitrobenzyloxycarbonyl)guanidino]acetylamino]pyrrolidine ½ sulfate (350 g, purity 86%) was added to a solution of concentrated sulfuric acid (234 g) and methanol (2.45 L) and the mixture was stirred at from 40 to 45° C. for 2.5 hours. The reaction mixture was cooled to from 20 to 30° C., and then was stirred at the same temperature for 0.5 hours. Diisopropyl ether (3.5 L) was added to the mixture, which was stirred at the same temperature for 1 hour. The crystals which precipitated were collected by filtration to give the title compound (328 g, purity 95.8%, yield 95.4%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07091363B2uspto-grants-2006_08