Acetic Acid → 6-(Benzenesulphonylmethyl)-2-(cyanomethylamino)-3-(furan-3-yl)benzoic acid

Participants

Reaction Conditions

Reaction Steps

A solution of 5-(benzenesulphonylmethyl)-8-(furan-3-yl)-1,2-dihydro-benzo[d][1,3]oxazin-4-one (Intermediate 210, 0.115 g) and sodium cyanide (0.03 g) in DMSO (4 ml) was stirred and heated at 60° C. for 2 hours. After cooling, the mixture was diluted with water, acidified with acetic acid and extracted with ethyl acetate. The organic layer was dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of DCM:methanol:water:acetic acid (350:20:3:2). The product was crystallized from DCM and cyclohexane to give 6-(benzenesulphonylmethyl)-2-(cyanomethylamino)-3-(furan-3-yl)benzoic acid (0.106 g).

Provenance & Evidence