Ammonia → HCID 58109716, compound

Participants

Reaction Steps

4-((S)-1-((R)-6-allyl-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-3-yl)ethyl)benzoic acid (12 mg, 0.03 mmol), ammonia in methanol (c.a. 7N, 1 mL, excess), HATU (12 mg, 1.1 equiv.), and DIEPA (11 μL, 2 equiv.) were mixed in 4:1 CH2Cl2 and DMF (2 mL). The mixture was stirred overnight at rt, diluted with EtOAc (5 mL), washed with 5% aq HCl (2×2 mL). The organic layer was concentrated and purified by prep HPLC to afford 4-((S)-1-((R)-6-allyl-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-3-yl)ethyl)benzamide (2 mg, 17.5%) product. LC-MS Method 1 tR=1.4 min, m/z=383 (M+1); 1H NMR (CDCl3) 7.55 (d, 2H), 7.25 (t, 2H), 7.03 (t, 2H), 6.94 (d, 2H), 6.03 (br d, 2H), 5.68 (m, 2H), 5.05 (dd, 2H), 2.95 (m, 1H), 1.54 (d, 3H).

Provenance & Evidence