Cyclopropaneacetic acid → N-(Cyclopropylacetyl)-L-alanine Methyl Ester

Reaction equation

[CH:1]1([CH2:4][C:5]([OH:7])=O)[CH2:3][CH2:2]1.Cl.[CH3:9][O:10][C:11](=[O:15])[C@H:12]([CH3:14])[NH2:13]>>[CH3:9][O:10][C:11](=[O:15])[C@H:12]([CH3:14])[NH:13][C:5](=[O:7])[CH2:4][CH:1]1[CH2:2][CH2:3]1

Participants

Reactant 2

HCID 138440Cyclopropaneacetic acid

HCID 2733257Alanine methyl ester hydrochloride

Product 1

HCID 53934383N-(Cyclopropylacetyl)-L-alanine Methyl Ester

Procedure

Following General Procedure A above using cyclopropylacetic acid (Aldrich) and L-alanine methyl ester hydrochloride (Sigma), the title compound was prepared as an oil. The reaction was monitored by tlc on silica gel (Rf=0.15 in 25% ethyl acetate/hexanes) and purification was by flash column chromatography using 25% ethyl acetate/hexanes as the eluant.

Workup

customThe reaction was monitored by tlc on silica gel (Rf=0.15 in 25% ethyl acetate/hexanes) and purification

Sources & evidence

ORD record: ord-0f0e1de8b7ee492c95e8d53e5344dce5
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07390801B2

Reaction notes

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