Water → HCID 57319928, compound

Participants

Reaction Steps

(3S)-3-[[N-tert-Butoxycarbonyl-(L)-phenylalanyl]amino]-2-hydroxytetrahydrofuran (0.1 g) was dissolved in acetic anhydride (3 ml) followed by addition of 4-dimethylaminopyridine (DMAP) (0,012 g) and the mixture was stirred at room temperature for 12 hours. The reaction mixture was then poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with 10% aqueous citric acid, water, saturated aqueous sodium hydrogen carbonate, and saturated aqueous sodium chloride in the order mentioned and dried (MgSO4) and the solvent was distilled off to give (3S)-2-acetoxy-3-[[N-tert-butoxycarbonyl-(L)-phenylalanyl]amino]tetrahydrofuran (chemical formula below) (0,035 g, 29%). This product was recrystallized from ethyl acetate-hexane. Colorless crystals, m.p. 156°-157° C. Optical rotation [α]D -49.9° (C=0.15, CHCl3). ##STR45##

Provenance & Evidence