Hydrochloric Acid → HCID 22804687, compound

Participants

Reaction Conditions

Reaction Steps

A solution of benzylamine (2.14 g, 0.02 moles) in water (25 ml) was adjusted to pH5 with 5N hydrochloric acid. 2-Deoxy-D-ribose (1.34 g, 0.01 mole) and sodium cyanoborohydride (0.062 g, 0.01 mole) were added and the solution was allowed to stand for 15 hours at room temperature. The pH of the solution was adjusted to 10 with sodium carbonate and the mixture was washed several times with ethyl acetate. The aqueous solution was cooled to 0° C, and phenyl chloroformate (1.7 g., 0.011 mmoles) in dioxan (15 ml) was added with stirring. After 3 hours at 0° C., the reaction was allowed to warm to room temperature, the pH was adjusted to 7 by the addition of 5N hydrochloric acid and the mixture was extracted with ethyl acetate. The organic extract was dried over magnesium sulphate and evaporated under reduced pressure to yield 1,2(S),3(S)-trihydroxy-5-[N-phenoxycarbonyl-N-benzylamino]pentane (2.1 g.) as an oil which slowly solidified on standing. δ (CDCl3 + D2O) 7.2 (10 H, m); 4,5 (2H, s); 3,5 (6 H,m) 1.8 (2H,m). νmax. (film) 3400, 1705, 1600 cm-1.

Provenance & Evidence