Formaldehyde → HCID 69037992, compound

Participants

Reaction Steps

Compound 39i-b (103 mg, 168 μmol) and 37% formaldehyde (50 μL, 1.8 mmol) were dissolved in MeOH (2 mL) and stirred for 3 h at room temperature. Sodium cyanoborohydride (16 mg, 252 μmol) was added and the mixture was stirred for 2 h. The reaction was diluted with EtOAc (400 mL), washed with saturated NaHCO3 (3×150 mL) and brine (100 mL), dried over Na2SO4, filtered, and evaporated. The residue was purified by CombiFlash chromatography (silica, 0–10% CH2Cl2/MeOH) and then lyophilized from CH3CN/H2O to give title compound (77 mg, 74%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 7.90–7.82 (m, 2H), 7.71 (s, 1H), 7.68–7.42 (m, 6H), 4.15–3.92 (m, 3H), 3.80–3.00 (m, 7H), 2.71–2.10 (m, 9H), 1.93–1.40 (m, 9H), 1.17–0.95 (m, 6H); 19F NMR (282 MHz, CDCl3) δ −62.9; ESI MS m/z 623 [C32H41F3N2O5S+H]+.

Provenance & Evidence