Ethyl bromoacetate → HCID 69587923, compound

Participants

Reaction Steps

To a mixture of the (3-aminophenyl)carbamic acid tert-butyl ester (100 mg, 0.48 mmol) and 2-mercaptonicotinic acid (81 mg, 0.52 mmol) in DMF (5 mL) was added EEDQ (154 mg, 0.63 mmol). The mixture was stirred at ambient temperature for 15 h, was diluted with water and extracted with ethyl acetate (3×25 mL). The combined extracts were washed with water and brine and dried over magnesium sulfate. The residue was taken up in a small quantity of ethyl acetate (3 mL) and was briefly heated at reflux (1 minute). The mixture was cooled and the resulting solids collected via vacuum filtration on a fritted glass funnel. This afforded 90 mg of a solid which was not purified or characterized, but carried on directly. The material was dissolved in NMP (5 mL) and was treated with ethyl bromoacetate (32 μL, 0.29 mmol) and DIPEA (90 μL, 0.52 mmol). The resulting mixture was stirred for 10 minutes and was poured into water. The resulting mixture was extracted with ethyl acetate (3×50 mL) and the combined extracts were washed with water and brine. Filtration and concentration in vacuo afforded a residue which was purified via radial chromatography (1 mm plate, 10% ethyl acetate/hexanes) to give 41 mg (36%) of [5-(3-tert-butoxycarbonylamino-phenylcarbamoyl)pyrdin-2-ylsulfanyl]acetic acid ethyl ester as a solid: 1H NMR (300 MHz, acetone-d6) δ 9.63 (bs, 1H), 8.99 (m, 1H), 8.45 (bs, 1H), 8.18 (m, 1H), 8.01 (s, 1H), 7.58 (m, 1H), 7.40 (m, 1H), 7.20 (m, 2H), 4.13 (m, 2H), 4.07 (s, 2H), 1.47 (s, 9H), 1.19 (m, 1H); MS (EI) m/z 430.06 (M−H)−.

Provenance & Evidence