Acetyl chloride → HCID 86675915, compound

Participants

Reaction Steps

To a stirred solution of 6-((S)-5-((2R,5R)-5-(aminomethyl)-1,4-dioxan-2-yl)-4,5-dihydroisoxazol-3-yl)-N-(4-fluoro-3-methoxybenzyl)-2-methylpyrimidine-4-carboxamide (0.08 g, 0.174 mmol, Preparation #J.1) in DCM (5 mL) at 0° C., was added TEA (0.073 mL, 0.522 mmol, Spectrochem) followed by acetyl chloride (0.015 mL, 0.209 mmol, Spectrochem). The reaction mixture was stirred for 30 min, was diluted with DCM (30 mL) and washed with water (2×20 mL). The organic layer dried over sodium sulphate and concentrated under reduced pressure. The resulting crude material was purified by preparative TLC eluting with 60% EtOAc in hexane to afford 6-((S)-5-((2R,5R)-5-(acetamidomethyl)-1,4-dioxan-2-yl)-4,5-dihydroisoxazol-3-yl)-N-(4-fluoro-3-methoxybenzyl)-2-methylpyrimidine-4-carboxamide 0.065 g (74%); 1H NMR (400 MHz, DMSO): δ 9.50 (t, J=5.6 Hz, 1H), 8.13 (s, 1H), 7.93 (t, J=5.6 Hz, 1H), 7.17-7.11 (m, 2H), 6.89-6.81 (m, 1H), 4.81-4.75 (m, 1H), 4.48 (d, J=6.4 Hz, 2H), 3.88-3.86 (m, 1H), 3.81 (s, 3H), 3.78-3.63 (m, 2H), 3.46-3.36 (m, 4H), 3.32-3.22 (m, 2H), 3.08-3.00 (m, 2H) 2.75 (s, 3H), 1.79 (s, 3H); LC/MS (Table 1, Method e) Rt=2.69 min; MS: m/z 502 (m+H)+.

Provenance & Evidence