Reaktion #2317480

ord-63356514b1d9420aa0e377ab74737d7a

Reaktionsgleichung

CC(C)[C@H](NC(=O)N1CCCCCC1)C(=O)O
AC
CC(C)(C)OC(=O)[C@@H](N)Cc1ccc(OCc2ccccc2)cc1
product
CC(C)(C)OC(=O)[C@@H](N)Cc1ccc(OCc2ccccc2)cc1
(S)-2-Amino-3-(4-benzyloxy-phenyl)-propionic acid tert-butyl ester
→
CC(C)C(NC(=O)N1CCCCCC1)C(=O)NC(Cc1ccc(OCc2ccccc2)cc1)C(=O)OC(C)(C)C
title compound
Ausbeute 48.2%
CC(C)C(NC(=O)N1CCCCCC1)C(=O)NC(Cc1ccc(OCc2ccccc2)cc1)C(=O)OC(C)(C)C
2-{2-[(Azepane-1-carbonyl)-amino]-3-methyl-butyrylamino}-3-(4-benzyloxy-phenyl)-propionic acid tert-butyl ester
Ausbeute 48.2%

Edukte

CC(C)[C@H](NC(=O)N1CCCCCC1)C(=O)O
AC
CC(C)(C)OC(=O)[C@@H](N)Cc1ccc(OCc2ccccc2)cc1
product
CC(C)(C)OC(=O)[C@@H](N)Cc1ccc(OCc2ccccc2)cc1
(S)-2-Amino-3-(4-benzyloxy-phenyl)-propionic acid tert-butyl ester

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe crude reaction product
  2. 2
    Sonstigewas purified by chromatography (silica gel, EtOAc)

Vorschrift

A solution of the product from Example AC ((S)-2-[(azepane-1-carbonyl)-amino]-3-methyl-butanoic acid) (0.50 g, 2.07 mmol) and the product from Example A ((S)-2-amino-3-(4-benzyloxy-phenyl)-propionic acid tert-butyl ester) (0.67 g, 2.07 mmol) were coupled according to the procedure described in Example AH. The crude reaction product was purified by chromatography (silica gel, EtOAc) to give the title compound as a white foam (0.55 g, 48%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06423689B1uspto-grants-2002_07