Methanol → tert-butyl [1-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-(methylsulfonyl)butan-2-yl]carbamate

Participants

Reaction Steps

To a solution of tert-butyl [1-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-(methylsulfanyl)butan-2-yl]carbamate (29 g, 80 mmol) in methanol (700 mL) was added Oxone (148 g, 0.241 mol) and water (700 mL) at room temperature. After 3 hours, the reaction mixture was quenched with 20% aqueous sodium bisulfate solution, diluted with water, and extracted with DCM. The combined organics were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give tert-butyl [1-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-(methylsulfonyl)butan-2-yl]carbamate which was used in the next step without purification. MS ESI calc'd. for C18H25N2O6S [M+H]+ 397. found 397. 1H NMR (400 MHz, CD3OD) δ 7.87-7.82 (m, 4H), 4.05-3.95 (m, 1H), 3.77-3.75 (m, 2H), 3.25-3.10 (m, 2H), 3.00 (s, 3H), 2.11-1.89 (m, 2H), 1.24 (s, 9H).

Provenance & Evidence