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 36976Notes

Reaction equation

HRID 36976 reaction equation
C(C1N(C2C(F)=CC=CC=2Cl)C(C=O)=C(C)N=1)CCC.[H-].[Na+].C(COC)OC.C(C1N(CC2C(F)=CC=CC=2Cl)C(/C(/C)=C(/C2SC=CC=2)\C(O)=O)=CN=1)CCC.[CH2:58]([C:62]1[N:63]([CH2:79][C:80]2[C:85]([F:86])=[CH:84][CH:83]=[CH:82][C:81]=2[Cl:87])[C:64](/[CH:67]=[C:68](\[CH2:73][C:74]2[S:75][CH:76]=[CH:77][CH:78]=2)/[C:69]([O:71]C)=[O:70])=[CH:65][N:66]=1)[CH2:59][CH2:60][CH3:61]>C(OCC)(=O)C.CCCCCC>[CH2:58]([C:62]1[N:63]([CH2:79][C:80]2[C:85]([F:86])=[CH:84][CH:83]=[CH:82][C:81]=2[Cl:87])[C:64](/[CH:67]=[C:68](\[CH2:73][C:74]2[S:75][CH:76]=[CH:77][CH:78]=2)/[C:69]([OH:71])=[O:70])=[CH:65][N:66]=1)[CH2:59][CH2:60][CH3:61]

Participants

8

Reactant 5

HCID 80711,2-DimethoxyethaneHCID 24758Sodium hydrideHCID 86746469methyl (E)-[2-n-butyl-1-{(2-chloro-6-fluorophenyl)methyl}-1H-imidazol-5-yl]-2-(2-thienyl)methyl-2-propenoateHCID 867465472-n-Butyl-1-(2-chloro-6-fluorophenyl)-methyl-1H-imidazole-5-carboxaldehydeHCID 86748679(E)-3-[2-n-Butyl-1-{(2-chloro-6-fluoro-phenyl)methyl}-1H-imidazol-5-yl]-2-(2-thienyl)-methyl-2-propenoic Acid

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 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

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 hexane 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-e28e109cd07a41d984b4c2d123d8b171
Source dataset
uspto-grants-1995_05
Patent number
US05418250

Reaction notes

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