Sodium Hydroxide → HCID 67915583, compound

Participants

Reaction Steps

1.7 g (3.5 mmol) of t-butyl (4S,5S)-4-(cyclohexylmethyl)-5-[(S,E)-5-(ethoxycarbonyl)-2-isopropyl-4-pentenyl]-2,2-dimethy--3-oxazolidinecarboxylate are dissolved in 20 ml of dioxan and treated with 7 ml (7.0 mmol) of 1N sodium hydroxide solution. Thereafter, the reaction mixture is stirred at 90° for 2.5 hours, cooled and poured into ice-water. Then, the reaction mixture is adjusted to pH 3 with a pH 2 buffer of potassium hydrogen sulphate and potassium sulphate and extracted with methylene chloride. The methylene chloride extracts are dried over magnesium sulphate and evaporated under reduced pressure. Chromatography of the residue on 18 g of silica gel with a mixture of methylene chloride and isopropanol as the eluting agent yields 1.28 g of (E,S)-5-[[(4S,5S)-3-(t-butoxycarbonyl)-4-(cyclohexylmethyl)-2,2-dimethyl-5-oxazolidinyl]methyl]-6-methyl-2-heptenoic acid as an oil, MS: 436 (M-CH3)+.

Provenance & Evidence