Triphosgene → HCID 118061548, compound

Participants

Reaction Steps

To a solution of Intermediate 334B (30.3 mg, 0.204 mmol) and TEA (0.142 mL, 1.018 mmol) in THF (8 mL) was added triphosgene (54.4 mg, 0.183 mmol) at 0° C. and the reaction mixture was stirred for 30 min at the same temperature. A solution of Intermediate 185B (60 mg, 0.204 mmol) in THF (1 mL) was added and the reaction mixture was stirred at RT for 12 h. The reaction mixture was diluted with water and extracted with ethyl acetate (3×15 mL). The combined organic layer was dried over sodium sulfate, filtered and the filtrate concentrated. The crude product was purified by preparative HPLC to afford Compound 334 as an off-white solid (20.6 mg, 23%). HPLC retention time 7.12 and 7.33 min (Methods B and C respectively). MS(ES): m/z=433 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.86 (dd, J=7.28, 2.26 Hz, 1H), 7.65-7.72 (m, 2H), 7.44-7.51 (m, 1H), 7.17-7.41 (m, 2H), 4.79 (s, 2H), 4.16-4.23 (m, 3H), 3.81-3.96 (m, 5H), 2.40-2.49 (m, 2H).

Provenance & Evidence