Water → HCID 90047129, compound

Participants

Reaction Steps

Compound 42a (117 mg, 0.34 mmol), pivalaldehyde (57.8 mg, 0.67 mmol), sodium triacetoxyborohydride (27.4 mg, 0.13 mmol), and acetic acid (0.123 μl, 2.15 μmol) were stirred in dichloromethane (0.05 mL) at rt for 24 h. H2O was added, followed by CH2Cl2. The organic layer was separated, dried over sodium sulfate, filtered, concentrated under reduced pressure and purified by preparative HPLC (HPLC method D) to give Compound 42b (60 mg, 43% yield) as a tan film. LCMS ESI 419.1 (M+MeOH+H), RT=1.80 min (Method B). 1H NMR (500 MHz, CD3OD-d4) d 8.25 (d, J=1.65 Hz, 1H), 7.97-8.05 (m, 1H), 7.81 (dd, J=1.93, 8.53 Hz, 1H), 7.64-7.73 (m, 2H), 7.42-7.53 (m, 2H), 7.30-7.41 (m, 1H), 4.64-4.92 (m, 5H), 4.34-4.53 (m, 2H), 3.22-3.29 (m, 2H), 1.06 (s, 9H).

Provenance & Evidence