Reaktion #412402

ord-8969d3e9535d42e7aba4f1c6ec9df930

Reaktionsgleichung

c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenylphosphine
CCOC(=O)N=NC(=O)OCC
diethyl azodicarboxylate
[N-]=[N+]=N
hydrazoic acid
c1ccccc1
benzene
COC(=O)[C@H](CCSC)NC(=O)c1ccc(CO)cc1-c1ccccc1
resultant compound
COC(=O)[C@H](CCSC)NC(=O)c1ccc(CO)cc1-c1ccccc1
4-(Hydroxymethyl)-2-phenylbenzoyl methionine methyl ester
→
COC(=O)[C@H](CCSC)NC(=O)c1ccc(CN=[N+]=[N-])cc1-c1ccccc1
title product
COC(=O)[C@H](CCSC)NC(=O)c1ccc(CN=[N+]=[N-])cc1-c1ccccc1
4-(Azidomethyl)-2-phenylbenzoyl methionine methyl ester

Edukte

c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenylphosphine
CCOC(=O)N=NC(=O)OCC
diethyl azodicarboxylate
[N-]=[N+]=N
hydrazoic acid
c1ccccc1
benzene
COC(=O)[C@H](CCSC)NC(=O)c1ccc(CO)cc1-c1ccccc1
resultant compound
COC(=O)[C@H](CCSC)NC(=O)c1ccc(CO)cc1-c1ccccc1
4-(Hydroxymethyl)-2-phenylbenzoyl methionine methyl ester

Reagenzien

Keine

Lösungsmittel

C1CCOC1
tetrahydrofuran
C1CCOC1
THF

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigeevaporated
  2. 2
    Sonstigechromatographed on silica gel

Vorschrift

To triphenylphosphine (1.0 equivalent) in tetrahydrofuran (THF) at −78° C. is added diethyl azodicarboxylate (1.0 equivalent) in THF. To this mixture is added a solution of hydrazoic acid in benzene (2.0 equivalents) and then the resultant compound from Example 16D (1.0 equivalent). After one hour the mixture was warmed to room temperature, stirred until the reaction is judged complete by TLC analysis, evaporated and chromatographed on silica gel to afford the title product.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06221865B1uspto-grants-2001_04