Hydrochloric Acid → HCID 70245553, compound

Participants

Reaction Conditions

Reaction Steps

Dry HCl gas was bubled through a solution of 3-[[4(S)-(4-cyanophenyl)tetrahydro-3-methyl-2-oxo-2H-1,3-oxazin-6(R)-yl]acetyl]aminopropionic acid methyl ester (125 mg 0.35 mmol) in dry CHCl3 containing anhydrous methanol (23 mg, 0.70 mmol), cooled with salt ice-water bath, at 0° C. for 5 hrs. The resulting solution was then kept at 0° C. for 6 hrs and at 15° C. for 12 hrs. The flammable portion was removed and the residue was dissolved in anhydrous methanol (3 ml) followed by addition of ammonium bicarbonate (84 mg, 0.88 mmol). After stirring at rt for 4 hrs, the mixture was concentrated and purified by flush chromatography over silica gel using a mixture of methylene chloride and methanol as the eluent to give a white amorphous solid (85 mg, 64% yield).1H NMR (300 MHz, CD3OD) δ1.90 (m, 1H), 1.22(m, 2H), 2.50(t, 2H), 2.60(dd, 1H), 2.66(s, 3H), 3.40(m, 2H), 3.60(s, 3H), 4.80(m, 2H), 7.54(d, 2H), 7.84(d, 2H); MS (ESI) Calc. for (M+1)+: 377. Found: 377.

Provenance & Evidence