Reaktion #409918

ord-6b68f6f8cf8b4fccb2ce6827101e391b

Reaktionsgleichung

C[C@H](NC(=O)Cc1cccc([N+](=O)[O-])c1)C(=O)Oc1cc(Cl)c(Cl)cc1Cl
N-(3-nitrophenylacetyl)-L-alanine 2,4,5-trichlorophenyl ester
C[C@H](NC(=O)Cc1cccc([N+](=O)[O-])c1)C(=O)Oc1cc(Cl)c(Cl)cc1Cl
m-Nitrophenylacetyl-L-alanine 2,4,5Trichlorophenyl Ester
COC(=O)[C@@H](N)Cc1ccccc1.Cl
L-phenylalanine methyl ester hydrochloride
→
COC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](C)NC(=O)Cc1cccc([N+](=O)[O-])c1
title compound
COC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](C)NC(=O)Cc1cccc([N+](=O)[O-])c1
N-[N-(3-Nitrophenylacetyl)-L-alaninyl]-L-phenylalanine Methyl Ester

Edukte

—
EtOAc hexanes
C[C@H](NC(=O)Cc1cccc([N+](=O)[O-])c1)C(=O)Oc1cc(Cl)c(Cl)cc1Cl
N-(3-nitrophenylacetyl)-L-alanine 2,4,5-trichlorophenyl ester
C[C@H](NC(=O)Cc1cccc([N+](=O)[O-])c1)C(=O)Oc1cc(Cl)c(Cl)cc1Cl
m-Nitrophenylacetyl-L-alanine 2,4,5Trichlorophenyl Ester
COC(=O)[C@@H](N)Cc1ccccc1.Cl
L-phenylalanine methyl ester hydrochloride
—
solid

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigethe product was purified by silica gel chromatography

Vorschrift

Following General Procedure Z and using N-(3-nitrophenylacetyl)-L-alanine 2,4,5-trichlorophenyl ester (from Example D8 above) and L-phenylalanine methyl ester hydrochloride (Sigma), the title compound was prepared as a solid (mp=154-158° C.). The reaction was monitored by tlc (Rf=0.3 in 1:1 EtOAc/hexanes) and the product was purified by silica gel chromatography using 50-100% EtOAc/hexanes as the eluent.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06211235B1uspto-grants-2001_04