2-n-butyl 4-chloro 1-(2-chlorophenyl)methyl-5-hydroxymethyl-1H-imidazole → {1-(2-chlorophenyl)methyl-2-n butyl-1H-imidazol-5-yl}methyl-alpha-ethylphenylalanine methyl ester

HRID 6484Notes

Reaction equation

HRID 6484 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:20])[C:7]([CH2:11]O)=[C:8](Cl)[N:9]=1)[CH2:2][CH2:3][CH3:4].[CH3:21][O:22][C:23](=[O:35])[C@:24]([CH2:33][CH3:34])([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[NH2:25]>>[CH3:21][O:22][C:23](=[O:35])[C@:24]([CH2:33][CH3:34])([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[NH:25][CH2:11][C:7]1[N:6]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:20])[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:9][CH:8]=1

Participants

3

Reactant 2

HCID 130740952-n-butyl 4-chloro 1-(2-chlorophenyl)methyl-5-hydroxymethyl-1H-imidazoleHCID 53840745a-Ethylphenylalanine methyl ester

Product 1

HCID 53794162{1-(2-chlorophenyl)methyl-2-n butyl-1H-imidazol-5-yl}methyl-alpha-ethylphenylalanine methyl ester

Procedure

The procedure of Example 4 (i), Method A, was followed using a-ethylphenylalanine methyl ester in place of α-methyl-phenylalanine methyl ester to give N-[{1-(2-chlorophenyl)methyl-2-n butyl-1H-imidazol-5-yl}methyl-α-ethylphenylalanine methyl ester. Hydrolysis of the ester using the procedure of Example 2 (ii), followed by treatment with hydrochloric acid, gave the title compound as the dihydrochloride salt; mp 209°-211° C.

Sources & evidence

ORD record
ord-36b3c2ed1dbc482aa4b7a196ab5747d7
Source dataset
uspto-grants-1993_09
Patent number
US05248689

Reaction notes

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