Methyl 3-phenylpropionate → (E)-3-[2-n-Butyl-1-{(4-cyanophenyl)methyl}-1H-imidazol-5-yl]-2-benzyl-2-propenoic Acid

HRID 1033907Notes

Reaction equation

HRID 1033907 reaction equation
C(C1[NH:6]C(C=O)=C(CC2C=CC(C#N)=CC=2)N=1)CCC.[CH2:21]([C:25]1[N:26]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([C:39](OCC)=O)=[CH:35][C:34]=2Cl)[C:27]([CH:30]=O)=[CH:28][N:29]=1)[CH2:22][CH2:23][CH3:24].[C:45]1([CH2:51][CH2:52][C:53]([O:55]C)=[O:54])[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.[OH-].[Na+].C(=O)([O-])[O-].[K+].[K+]>>[CH2:21]([C:25]1[N:26]([CH2:32][C:33]2[CH:34]=[CH:35][C:36]([C:39]#[N:6])=[CH:37][CH:38]=2)[C:27](/[CH:30]=[C:52](\[CH2:51][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)/[C:53]([OH:55])=[O:54])=[CH:28][N:29]=1)[CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 5

HCID 7643Methyl 3-phenylpropionateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 199367892-n-Butyl-1-(4-carboethoxy-2-chlorobenzyl)imidazole-5-aldehydeHCID 178441598HCID 178441598, compound

Product 1

HCID 67849253(E)-3-[2-n-Butyl-1-{(4-cyanophenyl)methyl}-1H-imidazol-5-yl]-2-benzyl-2-propenoic Acid

Procedure

The title compound is prepared by the procedure of Example 27, using 2-n-butyl-[(4-cyanophenyl)methyl]imidazole-5-aldehyde, prepared by the method of Example 42 describing the preparation of 2-n-butyl-1-[(4-carboethoxy-2-chlorophenyl)methyl]imidazole-5-aldehyde, and methyl 3-phenylpropanoate, except, instead of basic hydrolysis of the ester with sodium hydroxide, potassium carbonate hydrolysis was employed.

Workup

  1. customprepared by the method of Example 42 describing

Sources & evidence

ORD record
ord-61c99a7af3bf48ddb3906d89c099ac76
Source dataset
uspto-grants-1994_05
Patent number
US05312828

Reaction notes

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