Sodium Hydroxide → HCID 69545603, compound

Participants

Reaction Conditions

Reaction Steps

200 mg (0.487 mmol) of N-tert-butoxycarbonyl-3-(4-alloxycarbonyl-2-aminophenylthio)-L-alanine methyl ester (96.7%) was added to a system consisting of 5 ml TBME and 20 ml buffer solution (0.1M sodium chloride; 3 mM sodium phosphate pH 7.0) under vigorous stirring at 40° C. 100 μl of Alcalase 2.4 L [a subtilisin Carlsberg from Novo Nordisk] was added and the pH maintained at 7.0 under vigorous stirring at 40° C. by the controlled addition (pH-static) of 0.1N sodium hydroxide solution. After a consumption 5.44 ml of titrating agent (112% of theory; after 17.4 h), the reaction mixture was washed with 25 ml TBME, acidified to pH 2.5 with IN HCl and extracted with 3×25 ml ethyl acetate. The combined organic phases were dried over sodium sulfate, the solvent evaporated and the residue dried on a high vacuum to give 190 mg (0.479 mmol; 98%) of the product acid in 94.5% HPLC-purity (area-%).

Provenance & Evidence