N-(3,4-dichlorophenyl)alanine → 3-(N'-(3,4-Dichlorophenyl)-D,L-alaninyl)amino-epsilon-caprolactam

HRID 411346

Reaction equation

HRID 411346 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C@H:10]([C:12]([OH:14])=O)[CH3:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[NH2:15][C@H:16]1[CH2:23][CH2:22][CH2:21][NH:20][C:18](=[O:19])[CH2:17]1>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][CH:10]([C:12]([NH:15][CH:16]2[CH2:23][CH2:22][CH2:21][NH:20][C:18](=[O:19])[CH2:17]2)=[O:14])[CH3:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 5491659N-(3,4-dichlorophenyl)alanineHCID 18603542(S)-4-Aminoazepan-2-one

Product 1

HCID 692684043-(N'-(3,4-Dichlorophenyl)-D,L-alaninyl)amino-epsilon-caprolactam

Procedure

Following General Procedure A above using N-(3,4-dichlorophenyl)-D,L-alanine (Example Q) and 3-(S)-amino-ε-caprolactam (Sigma), the title compound was prepared as a solid having a melting point of 199° C. The reaction was monitored by tlc on silica gel (Rf=0.4 in 50% ethyl acetate/hexanes) and purification was by preparative thin layer chromatography using 50% ethyl acetate/hexanes as the eluant.

Workup

  1. customThe reaction was monitored by tlc on silica gel (Rf=0.4 in 50% ethyl acetate/hexanes) and purification

Sources & evidence

ORD record
ord-1aa413bc62ae47ea967997be14cf5166
Source dataset
uspto-grants-2003_05
Patent number
US06559141B2

Linked notes

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