Trifluoroacetic acid → (E)-3-[2-n-Butyl-1-{(4-carbomethoxyphenyl)methyl}-1H-imidazol-5-yl]-2-(2-thienyl)methyl-2-propenoic Acid

HRID 36998Notes

Reaction equation

HRID 36998 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([O:21][CH3:22])=[O:20])=[CH:15][CH:14]=2)[C:7]([CH:10]=O)=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].C(C1N(CC2C=CC(C(OCC)=O)=CC=2Cl)C(C=O)=CN=1)CCC.[S:47]1[CH:51]=[CH:50][CH:49]=[C:48]1[CH2:52][CH2:53][C:54]([O:56]C(C)(C)C)=[O:55].C(C1N(CC2C=CC=CC=2Cl)C(/C(/C)=C(\C2C=CN=CC=2)/C(O)=O)=CN=1)CCC.FC(F)(F)C(O)=O>>[CH2:1]([C:5]1[N:6]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([O:21][CH3:22])=[O:20])=[CH:15][CH:14]=2)[C:7](/[CH:10]=[C:53](\[CH2:52][C:48]2[S:47][CH:51]=[CH:50][CH:49]=2)/[C:54]([OH:56])=[O:55])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 5

HCID 6422Trifluoroacetic acidHCID 10334966Methyl 4-[(2-butyl-5-formyl-1H-imidazol-1-YL)methyl]benzoateHCID 11310395t-Butyl 3-(2-thienyl)-propanoateHCID 199367892-n-Butyl-1-(4-carboethoxy-2-chlorobenzyl)imidazole-5-aldehydeHCID 86746549(E)-3-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-2-(4-pyridyl)-methyl-2-propenoic acid

Product 1

HCID 14952889(E)-3-[2-n-Butyl-1-{(4-carbomethoxyphenyl)methyl}-1H-imidazol-5-yl]-2-(2-thienyl)methyl-2-propenoic Acid

Procedure

The title compound was prepared using 2-n-butyl-1-[(4carbomethoxyphenyl)methyl]imidazole-5-aldehyde (prepared by the method described for the preparation of 2-n-butyl-1-[(4-carboethoxy-2-chlorophenyl)methyl]imidazole-5-aldehyde in Example 42) and t-butyl 3-(2-thienyl)-propanoate by the procedure of Example 1 (iv, Method B), except, instead of basic hydrolysis, trifluoroacetic acid hydrolysis of the t-butyl ester was employed; mp 217°-220° C.

Workup

  1. customprepared by the method

Sources & evidence

ORD record
ord-c4c8546c7774425b944f4c19b9eb3017
Source dataset
uspto-grants-1995_05
Patent number
US05418250

Reaction notes

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