L-Alanine ethyl ester → N-[(3,5difluorophenyl)acetyl]alanine Ethyl Ester

HRID 433544

Reaction equation

HRID 433544 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=O)[CH:5]=[C:6]([F:8])[CH:7]=1.[CH2:13]([O:15][C:16](=[O:20])[C@H:17]([CH3:19])[NH2:18])[CH3:14]>>[CH2:13]([O:15][C:16](=[O:20])[C@H:17]([CH3:19])[NH:18][C:10](=[O:12])[CH2:9][C:4]1[CH:5]=[C:6]([F:8])[CH:7]=[C:2]([F:1])[CH:3]=1)[CH3:14]

Participants

3

Reactant 2

HCID 76507L-Alanine ethyl esterHCID 1454243,5-Difluorophenylacetic acid

Product 1

HCID 54306296N-[(3,5difluorophenyl)acetyl]alanine Ethyl Ester

Procedure

Following General Procedure BG and using 3,5-difluorophenylacetic acid (Aldrich) and alanine ethyl ester (Aldrich), the title compound was prepared as a solid with a melting point of 93°-95° C. The reaction was monitored by tlc on silica gel (Rf=0.8 in EtOAC) and purification was by chromatography on silica gel using EtOAc as the eluant followed by recrystallization from 1-chlorobutane.

Workup

  1. customThe reaction was monitored by tlc on silica gel (Rf=0.8 in EtOAC) and purification
  2. customfollowed by recrystallization from 1-chlorobutane

Sources & evidence

ORD record
ord-7ff41ec8fea642aa9e1552d10baa1be8
Source dataset
uspto-grants-2003_12
Patent number
US06667305B1

Linked notes

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