Acetic Acid → HCID 86749419, compound

Participants

Reaction Steps

A solution of (S,E)-3-[[(1,1-Dimethylethyl)-diphenylsilyl]oxy]-4-[[2-[4-(4-fluorophenyl)-2-(1-methylethyl)-6-phenyl-3-pyridinyl]ethenyl]methoxyphosphinyl]butanoic acid, methyl ester (826 mg, 1.10 mmol) in THF (10 ml) was treated with HOAc (320 ul, 336 mg, 5.6 mmol) and tetra-n-butylammonium fluoride (1.0M in THF, 3.3 ml, 3.3 mmol). After stirring at room temperature for 22 hours, the solution was poured into saturated NaHCO3 and extracted with EtOAc. The EtOAc extract was washed with brine, dried (Na2 SO4), filtered, and stripped to give an oil which was subsequently chromatographed (flash, Merck SiO2, 30% acetone in hexane followed by 50% acetone in hexane). (S,E)-4-[[2-[4-(4-Fluorophenyl)-2-(1-methylethyl)-6-phenyl-3-pyridinyl]ethenyl]methoxyphosphinyl]-3-hydroxybutanoic acid, methyl ester (497 mg, 88%) was obtained as a white oily foam.

Provenance & Evidence