Acetic Acid → {(2S)-2-(3,4-Dichlorophenyl)-4-[3-(1-oxidothiomorpholin-4-yl)azetidin-1-yl]butyl}methylamine diacetate

Participants

Reaction Steps

[(2S)-2-(3,4-Dichlorophenyl)-4-(3-thiomorpholin-4-ylazetidin-1-yl)butyl]methylamine hydrochloride (see Method 1; 270 mg, 0.54 mmol) was dissolved in acetic acid and to the resultant solution was added hydrogen peroxide (0.05 mL of 35% aqueous solution, 0.54 mmol). The mixture was stirred at room temperature for 2.5 h and the solvent was removed by evaporation. The residue was dissolved in ethanol (50 mL) and to the resultant solution was added MP-Carbonate resin (0.86 g of 3.18 mmol/g polymer-bound resin). The mixture was stirred for 30 min and then filtered whereupon the solvent was removed by evaporation. The product was purified by reversed phase chromatography using a mixture of acetonitrile and 0.1 M ammonium acetate aq. There was obtained 140 mg (49%) of {(2S)-2-(3,4-Dichlorophenyl)-4-[3-(1-oxidothiomorpholin-4-yl)azetidin-1-yl]butyl}methylamine diacetate. 1H NMR (400 MHz, CDCl3): 1.6-1.8 (m, 2H), 1.9 (s, 6H), 2.3-2.4 (m, 1H), 2.4-2.5 (m, 7H), 2.7-3.0 (m, 10H), 3.1 (m, 1H), 3.6 (m, 2H), 7.0 (dd, 1H), 7.2 (d, 1H), 7.3 (d, 1H), 8.2 (s, 2H); LCMS: m/z 404 (M+1)+.

Provenance & Evidence