1,2-Dichloroethane → HCID 86746082, compound

Participants

Reaction Steps

A mixture of 0.55 g (1.26 mmol) of (S)-5-[(4S,5S)-3-(t-butoxycarbonyl)-4-(cyclohexylmethyl)-2,2-dimethyl-5-oxazolidinyl]-4-isopropyl-2-pentenoic acid, 0.22 g (1.6 mmol) of HOBT, 0.14 ml (1.4 mmol) of butylamine and 8 ml of methylene chloride is cooled to 0° and treated dropwise with a solution of 0.29 g (1.5 mmol) of EDC in 2 ml of dimethylformamide. Thereafter, the reaction mixture is stirred at 0° for 1 hour and subsequently at room temperature for 16 hours and then poured into ice-water and extracted with methylene chloride. The methylene chloride extracts are dried over potassium carbonate and evaporated under reduced pressure. Chromatography of the residue obtained on 10 g of silica gel with a mixture of methylene chloride and isopropanol as the eluting agent yields 0.53 g of t-butyl (4S,5S)-5-[(S,E)-4-(butylcarbamoyl)-2-isopropyl-3-butenyl]-4-(cyclohexylmethyl)-2,2-dimethyl-3-oxazolidinecarboxylate as a pale yellow oil which is used directly in the next step without further purification.

Provenance & Evidence