Potassium Carbonate → HCID 69489700, compound

Participants

Reaction Steps

To a solution of 96 mg (0.25 mmol) {2-[(5-Hydroxy-benzo[b]thiophene-2-carbonyl)-amino]-phenyl}-carbamic acid tert-butyl ester (4) in 3 ml ethyl acetate was added 140 mg potassium carbonate and 60 mg (0.40 mmol) tert-butyl chloroacetate. The reaction mixture was heated at reflux for 16 h and poured into a saturated aqueous solution of ammonium chloride. The aqueous phase was extracted with ethyl acetate and the organic phase was dried over sodium sulfate, the solvent was evaporated and the residue subjected to silica gel chromatography (petrolether/ethyl acetate 4:1). The product fraction was recrystallized from heptane/diethylether to yield 57 mg (0.114 mmol) [2-(2-tert-Butoxycarbonylamino-phenylcarbamoyl)-benzo[b]thiophen-5-yloxy]-acetic acid tert-butyl ester (46), mp. 166° C.

Provenance & Evidence