m-Chloroperbenzoic acid → HCID 178476875, compound

Participants

Reaction Conditions

Reaction Steps

A solution of diethyl(4-{[4-{[7-(trans-4-hydroxycyclohexyl)-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate (100.0 mg, 0.15 mmol), di(tert-butyl)N,N-diethylphosphoramidite (367.9 mg, 1.48 mmol), and 1H-tetrazole (113.7 mg, 1.62 mmol) in DCM (5 mL) was stirred at rt for 18 h. The mixture was then cooled to −78° C. and mCPBA (43.65 mg, 0.18 mmol) was added. The resulting mixture was allowed to warm to rt during 1 h, and stirred for another 14 h. The mixture was concentrated in vacuo and the residue was purified by silica gel chromatography (5% 7 N ammonia in MeOH in DCM) to afford 38.5 mg of the desired product. 1H NMR (CDCl3, 400 MHz): δ=1.27 (t, J=7.2 Hz, 6H), 1.51 (s, 18H), 1.60-1.71 (m, 4H), 1.90-1.93 (m, 2H), 2.30-2.32 (m, 2H), 2.52 (dt, J=2.4, 7.2 Hz, 1H), 3.18 (d, J=21.60 Hz, 2H), 3.22 (s, 3H), 3.93 (s, 3H), 4.00-4.09 (m, 4H), 4.38 (s, 2H), 6.88 (dt, J=2.0, 8.4 Hz, 1H), 6.95 (t, J=2.0 Hz, 1H), 7.32 (d, J=8.8 Hz, 1H), 7.65 (s, 1H), 8.28 (d, J=7.6 Hz, 1H), 8.39 (s, 1H), 8.64 (d, J=8.8 Hz, 1H), 10.51 (s, 1H). MS (ES+): m/z 870.39 [MH+]. HPLC: tR=4.67 min (ZQ3, polar—5 min).

Provenance & Evidence