Water → HCID 9881077, compound

Participants

Reaction Steps

To a solution of 150 mg (0.50 mmol) of 7,8-dimethoxy-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one XXIIaa in 5 ml of DMF, add at 0° C. under an inert atmosphere 21 mg (0.52 mmol) of 60% NaH in oil. Stir at room temperature for 1 hour. Add at 0° C., 53 mg (0.60 mmol) of ethylene carbonate. Stir at room temperature overnight. Add 50 ml of H2O and extract three times with 50 ml of AcOEt; dry on MgSO4, evaporate the AcOEt and purify by silica chromatography (AcOEt 3/hexane 1, then AcOEt). Recrystallize in CHCl3/cHexane. Yield: 40%. M: 128–130° C. 1H-NMR (DMSO, 300 MHz): d 3.36–3.52 (m, 2H, HOCH2), 3.60 (s, 3H, OCH3), 3.70–3.86 (m, 5H, NCH2+OCH3), 4.11 (AB system, ? d=0.77, JAB=9.96, 2H, CH2), 4.77 (m, 1H, OH), 6.60 (s, 1H Ar), 7.39 (s, 1H Ar), 7.42–7.58 (m, 4H Ar). Mass: (M+H)+=341.16.

Provenance & Evidence