Potassium Carbonate → HCID 54268157, compound

Participants

Reaction Steps

(2S,3S)-2-Acetoxy-3-[[N-(1-naphthylcarbamoyl)-(L)-leucyl]amino]tetrahydrofuran (2.9 g) was suspended in methanol (50 ml) followed by addition of a solution of potassium carbonate (0.94 g) in water (5 ml) under ice-cooling and the mixture was stirred at room temperature for 1 hour. The reaction mixture was then poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4) and the solvent was distilled off to give 2-hydroxy-3-[[N-(1-naphthylcarbamoyl)-(L)-leucyl]amino]tetrahydrofuran (chemical formula below) (1.95 g, 72%). As recrystallized from dichloromethane-methanolisopropyl ether, colorless crystals, m.p. 177°-178° C., optical rotation [α]D +29.5° (c=0.25, dimethyl sulfoxide).

Provenance & Evidence