Acetic Acid → HCID 73057217, compound

Participants

Reaction Steps

Sodium cyanoborohydride (5.14 mg, 81.8 μmol, Eq: 1.50) was added to a solution of (S)-N-((S)-5-((6-bromo-2-methoxynaphthalen-1-yl)methyl)-4-oxo-2′,3′,4,5,5′,6′-hexahydro-3H-spiro[benzo[b][1,4]oxazepine-2,4′-pyran]-3-yl)-2-amino-propanamide (31 mg, 54.5 μmol, Eq: 1.00), glycolaldehyde dimer (3.6 mg, 30.0 μmol, Eq: 0.55) and acetic acid (3.27 mg, 3.15 μl, 54.5 μmol, Eq: 1.00) in MeOH (1 mL) and the mixture was stirred at RT overnight. The mixture was diluted with 1 N HCl and H2O/1 N NaOH was added to adjust the pH to ˜8-9. The mixture was extracted with EtOAc, the combined extracts were washed with brine, dried over Na2SO4 and concentrated. The resulting material was purified by flash chromatography to afford the title compound (30 mg, 90% yield). MS m/z 613.8 (MH+).

Provenance & Evidence