L-Alanine → HCID 18341177, compound

HRID 2299550Notes

Reaction equation

HRID 2299550 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C@H:4]([CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)[NH2:5].[Cl:14][C:15]1[CH:16]=[C:17]([NH:22][CH:23]([C:25](O)=[O:26])[CH3:24])[CH:18]=[CH:19][C:20]=1[Cl:21].N[C@H](C(O)=O)C>>[CH3:1][O:2][C:3](=[O:13])[C@H:4]([CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)[NH:5][C:25](=[O:26])[CH:23]([CH3:24])[NH:22][C:17]1[CH:18]=[CH:19][C:20]([Cl:21])=[C:15]([Cl:14])[CH:16]=1

Participants

4

Reactant 3

HCID 5950L-AlanineHCID 69164262-(3,4-Dichloro-phenylamino)-propionic AcidHCID 13833920Methyl 3-cyclohexyl-L-alaninate

Product 1

HCID 18341177HCID 18341177, compound

Procedure

Following General Procedure D and using 3-cyclohexylalanine methyl ester (prepared from β-cyclohexylalanine (Bachem) using General Procedure K) and N-(3,4-dichlorophenyl)-D,L-alanine, the title compound, as a mixture of diastereomers about alanine, was prepared as an oil. The reaction was monitored by tlc (Rf=0.27 (second isomer) and 0.30 (first isomer) in 35% EtOAc/hexanes) and purification was by flash chromatography (35% EtOAc/hexanes).

Sources & evidence

ORD record
ord-1f2f0e2671de4d1bacf391c2f2326216
Source dataset
uspto-grants-2002_12
Patent number
US06495693B2

Reaction notes

Loading…