Cyclohexaneacetic acid → N-(cyclohexyIacetyl)-L-alanine iso-butyl ester

HRID 322686Notes

Reaction equation

HRID 322686 reaction equation
[CH:1]1([CH2:7][C:8]([OH:10])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[CH2:12]([O:16][C:17](=[O:21])[C@H:18]([CH3:20])[NH2:19])[CH:13]([CH3:15])[CH3:14]>>[CH2:12]([O:16][C:17](=[O:21])[C@H:18]([CH3:20])[NH:19][C:8](=[O:10])[CH2:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[CH:13]([CH3:15])[CH3:14]

Participants

3

Reactant 2

HCID 21363Cyclohexaneacetic acidHCID 865849812-Methylpropyl (2S)-2-aminopropanoate hydrochloride

Product 1

HCID 54223838N-(cyclohexyIacetyl)-L-alanine iso-butyl ester

Procedure

Following General Procedure B′ above, and using cyclohexylacetic acid (Aldrich) and L-alanine iso-butyl ester hydrochloride (from Example B′ above), the title compound was prepared as a solid having a melting point of 92° C.-93° C. The reaction was monitored by tlc on silica gel (Rf=0.39 in 1:3 EtOAc:hexane) and purification was by extraction with Et2O followed by washes with aqueous K2CO3 and aqueous HCl.

Sources & evidence

ORD record
ord-7f9736c151694ff493d6aae36645b89b
Source dataset
uspto-grants-2001_04
Patent number
US06211235B1

Reaction notes

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