Cyclopentylacetic acid → N-(cyclopentylacetyl)-L-alanine

Reaction equation

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

Participants

Reactant 2

HCID 71606Cyclopentylacetic acid

HCID 2733257Alanine methyl ester hydrochloride

Product 1

HCID 29895597N-(cyclopentylacetyl)-L-alanine

Procedure

Following General Procedure II-E above using cyclopentylacetic acid (Aldrich) and L-alanine methyl ester hydrochloride (Sigma), the title compound was prepared as a solid having a melting point of 43-46° C. Purification was by recrystallization from ethyl acetate/hexanes.

Workup

customPurification
customwas by recrystallization from ethyl acetate/hexanes

Sources & evidence

ORD record: ord-67b0e0ea560741a29465b3e78fa61211
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06849650B2

Reaction notes

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