L-(+)-Cysteine → Fudosteine

Participants

Reaction Steps

The compound was prepared in a similar manner to that described by J. F. Carson, et al, J. Org. Chem., 1964, 29, 2203. To a solution of sodium (6.44 g, 0,281 mol) in liquid ammonia (300 mL) was added cysteine (15.0 g, 62.5 mmol) over a 30 minutes period until permanent discharge of blue. Bromopropanol (15,8 mL, 0.175 mol) was added dropwise over 1 hour. The ammonia was allowed to evaporate and the resulting solid was dissolved in 1M HCl and passed through a column of Dowex 50 (H+) (5×30 cm) eluting with 1N ammonium hydroxide. Lyopholyzation yielded 21.3 g of the title compound as a white solid. MS(CI) m/e 180 (M+H)+. 1H NMR (DMSO-d6, 300 MHz) δ1.70-2.00 (m, 3H), 2.70 (t, J=7.5 Hz, 2H), 3.00-3.21 (m, 3H), 3.58-3.84 (m, 3H), 3.93 (dd, 1H).

Provenance & Evidence