m-Chloroperbenzoic acid → HCID 90281530, compound

Participants

Reaction Steps

Compound 36B (30 mg, 0.039 mmol) was dissolved in 3 mL of CH2Cl2 and to it was added m-CPBA (17.5 mg, 77%, 0.078 mmol). The reaction mixture was allowed to stir at rt for 20 min. To the reaction mixture was added N,N-diisopropylethylamine (0.2 mL, 0.017 mmol) and 3-methylazetidin-3-ol hydrochloride (34 mg, 0.39 mmol). The reaction mixture was allowed to stir at room temperature for 30 min and then partitioned between EtOAc and brine. The organic layer was separated, washed with brine and dried over Na2SO4 and concentrated. The residue was purified by RP-HPLC eluting with acetonitrile/H2O (with 0.1% TFA) to afford the title product. 1H NMR (400 MHz, methanol-d4) δ 8.53 (dd, 1H), 8.25 (d, 1H), 7.83 (m, 1H), 7.36-6.52 (m, 3H), 6.47-6.22 (m, 2H), 4.85 (m, 3H), 4.40-3.94 (m, 4H), 3.75-2.67 (m, 8H), 2.51 (m, 2H), 1.60 (s, 3H), 1.51-1.23 (m, 1H), 1.18-0.88 (m, 1H). MS (m/z): 808.01 [M+H]+.

Provenance & Evidence