Acetic Acid → HCID 86749425, compound

Participants

Reaction Steps

A solution of (S,E)-3-[[(1,1-Dimethylethyl)-diphenylsilyl]-oxy]-4-[[2-[4-(4-fluorophenyl)-2-(1-methylethyl)-3-quinolinyl]ethenyl]methoxyphosphinyl]butanoic acid, methyl ester (1.136 gm, 1.57 mmol) in THF (14 ml) was treated with HOAc (450 ul, 472 mg, 7.9 mmol) and tetra-n-butylammonium fluoride (1.0M in THF, 5.40 ml, 5.40 mmol). After stirring at room temperature for 18 hours, the solution was poured into saturated NaHCO3 and extracted with EtOAc. The EtOAc extract was washed with brine, dried (Na2SO4), filtered, and stripped to give an oil which was subsequently chromatographed (flash, Merck SiO2, 1:1 acetone:hexane). (S,E)-4-[[2-[4-(4-Fluorophenyl)-2-(1-methylethyl)-3-quinolinyl]-ethenyl]methoxyphosphinyl]-3-hydroxybutanoic acid, methyl ester (709 mg, 93%) was obtained as a colorless oil.

Provenance & Evidence