1,2-Dimethoxyethane → (E)-3-[2-n-butyl-1-{(2-chloro-6-fluorophenyl)methyl}-1H-imidazol-5-yl]-2-(2-thienyl)methyl-2-propenoic acid

HRID 1646122Notes

Reaction equation

HRID 1646122 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:12][C:13]2[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:20])[C:7]([CH:10]=O)=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].[H-].[Na+].C(COC)OC.C(C1N(CC2C(F)=CC=CC=2Cl)C(/C=C(/C2NN=NN=2)\[CH2:40][C:41]2[S:42][CH:43]=[CH:44][CH:45]=2)=CN=1)CCC.[C:60]([O:63]CC)(=[O:62])[CH3:61]>C(C1N(CC2C(F)=CC=CC=2Cl)C(/C=C(\CC2SC=CC=2)/C(OC)=O)=CN=1)CCC>[CH2:1]([C:5]1[N:6]([CH2:12][C:13]2[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:20])[C:7](/[CH:10]=[C:61](\[CH2:40][C:41]2[S:42][CH:43]=[CH:44][CH:45]=2)/[C:60]([OH:63])=[O:62])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 5

HCID 80711,2-DimethoxyethaneHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 199367632-n-Butyl-1-(2-chloro-6-fluorophenyl)methyl-1H-imidazole-5-carboxaldehydeHCID 178441611HCID 178441611, compound

Product 1

HCID 69947636(E)-3-[2-n-butyl-1-{(2-chloro-6-fluorophenyl)methyl}-1H-imidazol-5-yl]-2-(2-thienyl)methyl-2-propenoic acid

Reagents, catalysts & solvents 1

HCID 86746469methyl (E)-[2-n-butyl-1-{(2-chloro-6-fluorophenyl)methyl}-1H-imidazol-5-yl]-2-(2-thienyl)methyl-2-propenoateSolvent

Procedure

The procedure of Example 1, Method A, is used. 2-n-Butyl-1-(2-chloro-6-fluorophenyl)methyl-1H-imidazole-5-carboxaldehyde, trimethyl 3-(2-thienyl)-2-phosphonopropionate, sodium hydride and glyme are held at 60° C. for 1 hour to give, after chromatography over silica gel with 50% of hexanes in ethyl acetate, methyl (E)-[2-n-butyl-1-{(2-chloro-6-fluorophenyl)methyl}-1H-imidazol-5-yl]-2-(2-thienyl)methyl-2-propenoate and corresponding cis or (Z)-isomer. The (E)-isomer is hydrolyzed to afford (E)-3-[2-n-butyl-1-{(2-chloro-6-fluorophenyl)methyl}-1H-imidazol-5-yl]-2-(2-thienyl)methyl-2-propenoic acid.

Workup

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Sources & evidence

ORD record
ord-11c9f1ff21df4f198bf840078c3eeb8b
Source dataset
uspto-grants-1993_01
Patent number
US05177096

Reaction notes

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