Sodium hydride → HCID 18957769, compound

Participants

Reaction Steps

To a solution of 5-cyclopentyl-1,3-dihydro-3(R,S)-[(benzyloxycarbonyl)amino]-2H-1,4-benzodiazepin-2-one [Example 5, Step 3] (1.48 g, 3.93 mmol) in anhydrous dimethylformamide (40 ml), cooled in an ice bath, was added sodium hydride (60% dispersion in oil, 173 mg, 4.33 mmol) and the resulting mixture stirred under nitrogen for 1 h. Iodopropane (0.46 ml, 4.72 mmol) was then added and the mixture stirred at room temperature for 3 h. The solvent was evaporated and the residue partitioned between dichloromethane (100 ml) and water (100 ml). The aqueous layer was re-extracted with more dichloromethane (100 ml), the organic extracts were combined, dried (MgSO4) and evaporated. The residue was then triturated with ether to afford the title compound (1.36 g, 83%) as a white solid. mp 138°14 140° C. 1H NMR (360 MHz, CDCl3) δ 0.80 (3H, t, J=7.4 Hz), 1.26-1.79 (8H, m), 1.94 (1H, m), 2.12 (1H, m), 3.30 (1H, m), 3.55 (1H, m), 4.29 (1H, m), 5.10 (2H, m), 5.13 (1H, d), 6.52 (1H, d, J=8.1 Hz), 7.23-7.34 (5H, m), 7.48 (1H, t of d, J=8.0 and 1.4 Hz), 7.56 (1H, dd, J=7.8 and 1.4 Hz).

Provenance & Evidence