Reaktion #3800

ord-264b85044b034d0ba81c2947a44108fd

Reaktionsgleichung

CC(=O)Nc1ccc(SSc2ccc(NC(C)=O)cc2C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c(C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c1
2-{5-acetylamino-2-[4-acetylamino-2-(1-tert-butoxycarbonyl-3-methyl-butylcarbamoyl)-phenyldisulfanyl]-benzoylamino}-4-methyl-pentanoic acid tert-butyl ester
O=C(O)C(F)(F)F
trifluoroacetic acid
→
CC(=O)Nc1ccc(SSc2ccc(NC(C)=O)cc2C(=O)NC(CC(C)C)C(=O)O)c(C(=O)NC(CC(C)C)C(=O)O)c1
title compound
Ausbeute 77.3%
CC(=O)Nc1ccc(SSc2ccc(NC(C)=O)cc2C(=O)NC(CC(C)C)C(=O)O)c(C(=O)NC(CC(C)C)C(=O)O)c1
2-{5-Acetylamino-2-[4-acetylamino-2-(1-carboxy-3-methyl-butylcarbamoyl)-phenyldisulfanyl]-benzoylamino}-4-methyl-pentanoic acid
Ausbeute 77.3%

Edukte

CC(=O)Nc1ccc(SSc2ccc(NC(C)=O)cc2C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c(C(=O)NC(CC(C)C)C(=O)OC(C)(C)C)c1
2-{5-acetylamino-2-[4-acetylamino-2-(1-tert-butoxycarbonyl-3-methyl-butylcarbamoyl)-phenyldisulfanyl]-benzoylamino}-4-methyl-pentanoic acid tert-butyl ester
O=C(O)C(F)(F)F
trifluoroacetic acid

Reagenzien

Keine

Lösungsmittel

ClCCl
dichloromethane

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThis compound was prepared
  2. 2
    SonstigeThe crude product was recrystallized from dimethylformamide/water

Vorschrift

This compound was prepared according to the procedure described in Example 50 using [S-(R*,R*)]2-{5-acetylamino-2-[4-acetylamino-2-(1-tert-butoxycarbonyl-3-methyl-butylcarbamoyl)-phenyldisulfanyl]-benzoylamino}-4-methyl-pentanoic acid tert-butyl ester (0.2 g, 0.2 mmol) from Example 44, 10 mL dichloromethane, and 10 mL trifluoroacetic acid. The crude product was recrystallized from dimethylformamide/water to afford 0.1 g of the title compound, mp 241°-242° C.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05734081uspto-grants-1998_03