Water → Benzyloxycarbonyl-L-homocystine

Participants

Reaction Conditions

Reaction Steps

L-homocystine (5 g) was dissolved in a mixture (80 ml) of dioxane/H2O. At 0° C. and under stirring, 1.52 g (2.1 eq) of NaOH and a solution of 7.8 g (2.4 eq) of benzylchloroformate in 40 ml dioxane were added. The pH was maintained at 9 by addition of a solution of NaOH 1M. After stirring for 2.30 h at room temperature, 100 ml H2O were added and the white precipitate was extracted by Et20 (2×50 ml). The aqueous phase was acidified to pH 1 and the precipitate was extracted by EtOAc (4×80 ml). The organic phase was washed, dried over Na2SO4, filtered and evaporated in vacuo. White solid 10.2 g (100%).

Provenance & Evidence