2-(3,5-Dichlorophenyl)acetic acid → N-[(3,5-dichlorophenyl)acetyl]-L-alanine iso-butyl ester

HRID 1859153Notes

Reaction equation

HRID 1859153 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=O)[CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl.[CH2:14]([O:18][C:19](=[O:23])[C@H:20]([CH3:22])[NH2:21])[CH:15]([CH3:17])[CH3:16]>>[CH2:14]([O:18][C:19](=[O:23])[C@H:20]([CH3:22])[NH:21][C:10](=[O:12])[CH2:9][C:4]1[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=1)[CH:15]([CH3:17])[CH3:16]

Participants

3

Reactant 2

HCID 64524872-(3,5-Dichlorophenyl)acetic acidHCID 865849812-Methylpropyl (2S)-2-aminopropanoate hydrochloride

Product 1

HCID 22894972N-[(3,5-dichlorophenyl)acetyl]-L-alanine iso-butyl ester

Procedure

Following General Procedure F' above, and using 3,5-dichlorophenylacetic acid (from Example C' above) and L-alanine iso-butyl ester hydrochloride (from Example B' above), the title compound was prepared as a solid having a melting point of 115°-116° C. The reaction was monitored by tlc on silica gel (Rf=0.40 in 3% methanol/dichloromethane) and purification was by flash chromatography on silica gel using 3% methanol/dichloromethane as the eluant.

Sources & evidence

ORD record
ord-8aa4651f4b6b45ad82da73d73daea1a5
Source dataset
uspto-grants-2000_11
Patent number
US06153652

Reaction notes

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