(1-Methylcyclopropyl)methanol → N-[(3-chlorophenyl)acetyl]alanine (1-methylcyclopropyl)methyl ester

HRID 478812Notes

Reaction equation

HRID 478812 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([NH:11][C@H:12]([C:14]([OH:16])=[O:15])[CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH3:17][C:18]1([CH2:21]O)[CH2:20][CH2:19]1>>[CH3:17][C:18]1([CH2:21][O:15][C:14](=[O:16])[C@H:12]([CH3:13])[NH:11][C:9](=[O:10])[CH2:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[CH2:20][CH2:19]1

Participants

3

Reactant 2

HCID 137701(1-Methylcyclopropyl)methanolHCID 15481783N-(3-chlorophenylacetyl)alanine

Product 1

HCID 20613258N-[(3-chlorophenyl)acetyl]alanine (1-methylcyclopropyl)methyl ester

Procedure

Following General Procedure C above, and using N-(3-chloroph,enylacetyl alanine (from Example D above) and (1-methylcyclopropyl)methanol (Aldrich) the title compound can be prepared. The reaction was monitored by tlc on silica gel and purification was by liquid chromatography using 3:7 EtOAc:hexane as the eluant. NMR data was as follows:

Sources & evidence

ORD record
ord-14b0b2b745cf44b5a0df36d09dae0af5
Source dataset
uspto-grants-2003_11
Patent number
US06642261B2

Reaction notes

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