Stannous Chloride → HCID 86715465, compound

Participants

Reaction Conditions

Reaction Steps

Tin (II) chloride (499.4 mg, 2.213 mmol) was added to a stirred solution of tert-butyl N-tert-butoxycarbonyl-N-[5-(4-isopropylsulfonylphenyl)-3-[3-(4-nitrophenyl)isoxazol-5-yl]pyrazin-2-yl]carbamate (491 mg, 0.7376 mmol) in ethanol (15 mL) and the resulting solution heated at 60° C. for 16 h. The reaction mixture was cooled rt and concentrated in vacuo. The residue was partitioned between ethyl acetate (10 mL) and 1M NaOH(aq) (5 mL) and the residue that formed was filtered off. The layers were then separated and the aqueous layer was extracted further with ethyl acetate (2×10 mL) and the combined organic extracts were washed with brine (1×10 mL), dried over MgSO4 and concentrated in vacuo. The material was purified by column chromatography on silica (ISCO Companion, 12 g column) eluting with 0-100% EtOAc with petroleum ether. The product fractions were combined and concentrated in vacuo to leave the title compound as a yellow/orange solid (286 mg, 61% yield); 1H NMR (400 MHz, CDCl3) δ 1.37 (m, 6H), 1.42 (s, 18H), 3.28 (m, 1H), 3.95 (br s, 2H), 6.79 (m, 2H), 7.30 (s, 1H), 7.72 (d, J=8.0 Hz, 1H), 8.10 (m, 2H), 8.36 (m, 2H) and 9.06 (s, 1H) ppm; MS (ES+) 636.3 (M+H)

Provenance & Evidence