HCID 11341386, compound → HCID 11410077, compound

Participants

Reaction Conditions

Reaction Steps

Sodium perborate tetrahydrate (97 mg, 0.63 mmol) was added as a solid to a stirred solution of (2R)-3-(4′-indol-1-ylbiphen-4-ylmethylsulfanyl)-2-phenylacetylamino-propionic acid (300 mg, 0.58 mmol) in acetic acid (10 mL) at 40° C. This solution was stirred at 40° C. for 2 hours (HPLC control) and then diluted with ethyl acetate (50 mL), washed with water, brine (2×), dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification of the product by flash column chromatography, using 15% methanol in dichloromethane as eluent, afforded the title compound has an off-white solid (261 mg g, 84%) as a 1:1 mixture of diasereomers; 1H NMR (DMSO-d6, 300 MHz) δ 12.98 (1H, s, COOH), 8.75 and 8.80 (both 0.5H, d, J=8 Hz, NH), 8.40 (1H, d, J=8 Hz, NH), 7.84 (2H, m, Ar—H), 7.60-7.78 (7H, m, Ar—H), 7.44 and 7.39 (both 1H, d, J=8 Hz, Ar—H), 7.12-7.28 (7H, m, Ar—H), 6.72 (1H, d, J=3 Hz, Ar—H), 4.68 and 4.48 (both 0.5H, m, CHN), 4.16 (2H, m, PhCH2CO) 3.52 and 3.32 (both 1H, s, PhCH2S), 3.09 (1H, m, CHHCHN), 2.96 (1H, m, CHHCHN); ESI-LCMS e/z calcd for C32H28N2O4S 536.649, found 537 (M+H)+.

Provenance & Evidence