2-(3,5-Dichlorophenyl)acetic acid → 2-[(3,5-dichlorophenyl)acetamido]hexanoic Acid Methyl Ester

HRID 1016861Notes

Reaction equation

HRID 1016861 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.[CH3:14][O:15][C:16](=[O:23])[C@H:17]([CH2:19][CH2:20][CH2:21][CH3:22])[NH2:18]>>[CH3:14][O:15][C:16](=[O:23])[CH:17]([NH:18][C:10](=[O:12])[CH2:9][C:4]1[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=1)[CH2:19][CH2:20][CH2:21][CH3:22]

Participants

3

Reactant 2

HCID 64524872-(3,5-Dichlorophenyl)acetic acidHCID 14039065methyl (2S)-2-aminohexanoate hydrochloride

Product 1

HCID 179393142-[(3,5-dichlorophenyl)acetamido]hexanoic Acid Methyl Ester

Procedure

Following General Procedure F′ above, an using 3,5-dichlorphenylacetic acid (from Example C′ above) and L-norleucine methyl ester hydrochloride (Bachem), the title compound was prepared as a solid having a melting point of 77°-78° C. The reaction was monitored by tlc on silica gel (Rf=0.70 in 40% EtOAC/hexanes) and purification was by flash chromatography on silica gel using 40% EtOAc/hexanes as the eluant.

Workup

  1. customThe reaction was monitored by tlc on silica gel (Rf=0.70 in 40% EtOAC/hexanes) and purification

Sources & evidence

ORD record
ord-56678de076e14701854ed20400254452
Source dataset
uspto-grants-2002_11
Patent number
US06476263B1

Reaction notes

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