Hydrogen Peroxide → Ammonium Hydroxide

Participants

Reaction Steps

To a stirred solution of (2R)-5-({2-[(8R)-8-(3,5-difluorophenyl)-8-methyl-10-oxo-6,9-diazaspiro[4.5] dec-9-yl]ethyl}sulfanyl)-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (20.7 mg, 0.036 mmol, described in Example 20) in AcOH (0.50 mL) was added H2O2 (35% in H2O, 0.018 mL, 0.206 mmol). After 3 h, the reaction was quenched with saturated NaHCO3 solution (30 mL) and extracted with EtOAc (30 mL). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified on silica gel, eluting with a gradient of CH2Cl2:CH3OH:NH4OH—100:0:0 to 90:10:0.1, to afford the title compound. MS: m/z=591 (M+1). HRMS: m/z=591.2243; calculated m/z=591.2236 for C32H33F2N4O3S.

Provenance & Evidence