Lithium Hydroxide → HCID 86675919, compound

Participants

Reaction Steps

To a stirred solution of (S)-1-(((2R,5R)-5-((S)-3-(6-(4-fluoro-3-methoxybenzylcarbamoyl)-2-methylpyrimidin-4-yl)-4,5-dihydroisoxazol-5-yl)-1,4-dioxan-2-yl)methylamino)-1-oxopropan-2-yl acetate (0.11 g, 0.192 mmol) in ACN (3 mL) was added 2.5M lithium hydroxide (1.151 mL, 2.88 mmol) at RT. The reaction mixture was stirred for 3 h, diluted with EtOAc (25 mL) and washed with brine solution (2×15 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The resulting crude material was purified by preparative TLC eluting with 100% EtOAc to afford N-(4-fluoro-3-methoxybenzyl)-6-((S)-5-((2R,5R)-5-(((S)-2-hydroxypropanamido) methyl)-1,4-dioxan-2-yl)-4,5-dihydroisoxazol-3-yl)-2-methylpyrimidine-4-carboxamide 0.055 g (52%); 1H NMR (400 MHz, DMSO): δ 9.48 (t, J=6.4 Hz, 1H), 8.13 (s, 3H), 7.68 (t, 1H), 7.17-7.13 (m, 2H), 6.88 (m, 1H), 5.5 (d, J=4.8 Hz, 1H), 4.81-4.75 (m, 1H), 4.48 (d, J=6.0 Hz, 2H), 3.96-3.86 (m, 2H), 3.81 (s, 3H), 3.76-3.73 (m, 1H), 3.66-3.63 (m, 1H), 3.52-3.3.36 (m, 4H), 3.29-3.11 (m, 1H), 3.09 (m, 2H), 2.75 (s, 3H), 1.19 (d, J=6.8 Hz, 3H); LC/MS (Table 1, method c) Rt=2.89 min; MS: m/z 532 (m+H)+.

Provenance & Evidence