Tetrahydrofuran → HCID 118061732, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of Intermediate 308E (62.5 mg, 0.271 mmol) in toluene (2 mL) was added TEA (0.057 mL, 0.407 mmol), DPPA (0.062 mL, 0.271 mmol) and the reaction mixture was heated to 70° C. for 2 h. The reaction mass was cooled to RT and to it was added a solution of Intermediate 185B (40 mg, 0.136 mmol) in THF (1 mL) and the reaction mixture was stirred at RT for 12 h. The reaction mass was diluted with ethyl acetate (5 mL), the organic layer was separated, washed with a 10% aq. NaHCO3 solution, water, brine, dried over Na2SO4, filtered and the filtrate concentrated under vacuum. The crude compound was purified by preparative HPLC to afford Compound 308 as a pale yellow solid (54 mg, 75%). The HPLC Retention times are 2.339 min. and 2.344 min. (Methods J and K respectively); MS(ES): −m/z=522 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.82-7.88 (m, 1H), 7.77-7.82 (m, 1H), 7.61-7.72 (m, 1H), 7.47 (s, 3H), 7.30-7.41 (m, 1H), 7.14 (s, 3H), 4.72 (s, 2H), 4.08-4.18 (m, 2H), 3.78-3.88 (m, 2H), 3.10-3.22 (m, 4H).

Provenance & Evidence