L-Alanine ethyl ester → N-[(2-phenyl)-2-fluoroacetyl]alanine Ethyl Ester

HRID 23117

Reaction equation

[F:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([OH:5])=O.[CH2:12]([O:14][C:15](=[O:19])[C@H:16]([CH3:18])[NH2:17])[CH3:13]>>[CH2:12]([O:14][C:15](=[O:19])[C@H:16]([CH3:18])[NH:17][C:3](=[O:5])[CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[F:1])[CH3:13]

Participants

Reactant 2

HCID 76507L-Alanine ethyl ester

HCID 102649Fluorophenylacetic acid

Product 1

HCID 22894970N-[(2-phenyl)-2-fluoroacetyl]alanine Ethyl Ester

Procedure

Following General Procedure BF above, and using α-fluorophenyl acetic acid (Aldrich) and alanine ethyl ester (Aldrich), the title compound was prepared. The reaction was monitored by tlc on silica gel (Rf=0.75 in 1:1 EtOAc:hexane) and purification was by chromatography on silica gel using 1:2 ethyl acetate/hexanes as the eluent.

Workup

customThe reaction was monitored by tlc on silica gel (Rf=0.75 in 1:1 EtOAc:hexane) and purification

Sources & evidence

ORD record: ord-a20da671143b4668b7975ef86c4cd6a2
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06849650B2

Linked notes

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