1-Cyclohexene-1-acetic acid → N-[(cyclohex-1-enyl)acetyl]-L-alanine Iso-butyl Ester

HRID 1859156Notes

Reaction equation

HRID 1859156 reaction equation
[C:1]1([CH2:7][C:8]([OH:10])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH: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][C:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1)[CH:13]([CH3:15])[CH3:14]

Participants

3

Reactant 2

HCID 866991-Cyclohexene-1-acetic acidHCID 865849812-Methylpropyl (2S)-2-aminopropanoate hydrochloride

Product 1

HCID 54332828N-[(cyclohex-1-enyl)acetyl]-L-alanine Iso-butyl Ester

Procedure

Following General Procedure B' above, and using cyclohex-1-enyl acetic acid (Alfa) and L-alanine iso-butyl ester hydrochloride (from Example B' above), the title compound was prepared as a solid having a melting point of 49° C.-51° C. The reaction was monitored by tlc on silica gel (Rf=0.40 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-781ab91926834b3b934cedad6f085345
Source dataset
uspto-grants-2000_11
Patent number
US06153652

Reaction notes

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