m-Chloroperbenzoic acid → HCID 68752815, compound

Participants

Reaction Steps

Solid m-chloroperoxybenzoic acid (30 mg, about 50% titre, 0.10 mmol) was added to an ice-cooled solution of the product from Example 143D (37 mg, 0.093 mmol) in CHCl3 (7 mL). The yellow solution was stirred with ice cooling for 15 minutes, then transferred to a test tube and washed with 20% Na2CO3 (4 mL). The organic phase was concentrated under vacuum, and the residue purified by HPLC (30×100 mm XBridge column eluted with aqueous 0.1 M (NH4)2CO3-MeOH, 80:20-0:100 over 15 min), then by flash chromatography (silica gel eluted with EtOAc-MeOH, 100:0-80:20) to provide the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.38-1.54 (m, 1H), 1.64-1.86 (m, 4H), 1.90-2.23 (m, 3H), 2.30 (d, J=1.6 Hz, 3H), 2.38 (s, 3H), 3.34-3.49 (m, 2H), 3.88 (d, J=14.3 Hz, 1H), 7.22-7.31 (m, 1H), 7.34-7.48 (m, 2H), 8.39 (s, 1H), 8.42-8.55 (m, 1H), 9.51 (s, 1H); MS (ESI) m/z 415 (M+H)+.

Provenance & Evidence