Cyclopentylacetic acid → N-(cyclopentylacetyl)-L-alanine Iso-butyl Ester

HRID 428118

Reaction equation

HRID 428118 reaction equation
[CH:1]1([CH2:6][C:7]([OH:9])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[CH2:11]([O:15][C:16](=[O:20])[C@H:17]([CH3:19])[NH2:18])[CH:12]([CH3:14])[CH3:13]>>[CH2:11]([O:15][C:16](=[O:20])[C@H:17]([CH3:19])[NH:18][C:7](=[O:9])[CH2:6][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5]1)[CH:12]([CH3:14])[CH3:13]

Participants

3

Reactant 2

HCID 71606Cyclopentylacetic acidHCID 865849812-Methylpropyl (2S)-2-aminopropanoate hydrochloride

Product 1

HCID 54023872N-(cyclopentylacetyl)-L-alanine Iso-butyl Ester

Procedure

Following General Procedure B above, and using cyclopentylacetic acid (Aldrich) and L-alanine isobutyl ester hydrochloride (from Example B above), the title compound was prepared as a solid having a melting point of 62° C.-64° C. The reaction was monitored by tlc on silica gel (Rf=0.37 in 1:3 EtOAc:hexane) 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 (Rf=0.37 in 1:3 EtOAc:hexane) and purification
  2. extractionwas by extraction with Et2O

Sources & evidence

ORD record
ord-390d7096a46f4ae58cc66a46fa8b13ec
Source dataset
uspto-grants-2001_11
Patent number
US06313152B1

Linked notes

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