Potassium tert-butoxide → 3-[3-benzyloxy-4-(1,1,4-trioxo-[1,2,5]thiadiazolidin-2-yl)-benzyl]-3,4-dihydro-1H-benzo[1,4]diazepine-2,5-dione

Participants

Reaction Conditions

Reaction Steps

To a solution of the title N compound, N-[2-benzyloxy-4-(2,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[1,4]diazepin-3-ylmethyl)-phenyl]-N-[aminosulfonyl]-amino-acetic acid ethyl ester (93 mg, 0.168 mmol) in THF is cooled to 0° C. and treated dropwise with a solution of potassium t-butoxide in THF (1M, 0.244 mL, 0.244 mmol). After stirring at 0° C. for 30 min, additional potassium t-butoxide solution is added and stirring continued for another 1 h. The resulting suspension of fine solids is centrifuged, the supernatant is decanted and the cake of solids is suspended in EtOAc and centrifuged. The supernatant is decanted and the cake of solids is triturated with EtOAc and 2N aqueous HCl. The EtOAc layer is washed with brine, dried over anhydrous MgSO4, decolorized with charcoal, filtered and evaporated to give 3-[3-benzyloxy-4-(1,1,4-trioxo-[1,2,5]thiadiazolidin-2-yl)-benzyl]-3,4-dihydro-1H-benzo[1,4]diazepine-2,5-dione as a foam: [M+1]+=507.

Provenance & Evidence