(4-Chlorophenyl)acetic acid → N-[(4chlorophenyl)acetyl]-L-alanine Iso-butyl Ester

HRID 1884928Notes

Reaction equation

HRID 1884928 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.[CH2:12]([O:16][C:17](=[O:28])[C@H:18]([CH3:27])[NH:19]C(=O)CC(C)CC)[CH:13]([CH3:15])[CH3:14]>>[CH2:12]([O:16][C:17](=[O:28])[C@H:18]([CH3:27])[NH:19][C:9](=[O:11])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[CH:13]([CH3:15])[CH3:14]

Participants

3

Reactant 2

HCID 15880(4-Chlorophenyl)acetic acidHCID 15481764N-(3-methylpentanoyl)-L-alanine Isobutyl Ester

Product 1

HCID 15481765N-[(4chlorophenyl)acetyl]-L-alanine Iso-butyl Ester

Procedure

Following General Procedure B and using 4-chlorophenylacetic acid (Aldrich) and L-alanine iso-butyl ester hydrochloride (from Example 3 above), the title compound was prepared as a solid having a melting point of 111°-113° C. The reaction was monitored by tlc on silica gel and purification was by extraction with Et2O followed by washes with aqueous K2CO3 and aqueous HCl.

Workup

  1. customThe reaction was monitored by tlc on silica gel and purification
  2. extractionwas by extraction with Et2O

Sources & evidence

ORD record
ord-62fb7ed2e8b94361a727a31a7b17baea
Source dataset
uspto-grants-2004_07
Patent number
US06767918B2

Reaction notes

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