Acetic Acid → HCID 54216548, compound

Participants

Reaction Steps

1.7 g (3.7 mmol) of ethyl (S)-5-[(4S,5S)-3-(t-butoxycarbonyl)-4-(cyclohexylmethyl)-2,2-dimethyl-5-oxazolidinyl]-4-isopropyl-2-pentenoate are dissolved in 10 ml of methanol, treated with 2 ml (18 mmol) of 28% sodium hydroxide solution and stirred at room temperature for 16 hours. Thereafter, the reaction mixture is poured into ice-water, the pH value is adjusted to 5 with acetic acid and the mixture is extracted with ethyl acetate. The ethyl acetate extracts are dried over magnesium sulphate and evaporated under reduced pressure. Chromatography of the residue on 20 g of silica gel with a mixture of methylene chloride and isopropanol as the eluting agent yields 1.2 g of (S)-5-[(4S,5S)-3-(t-butoxycarbonyl)-4-(cyclohexylmethyl)-2,2-dimethyl-5-oxazolidinyl]-4-isopropyl-2-pentenoic acid as an oil, MS: 422 (M-CH3)+.

Provenance & Evidence