(Z)-tert-butyl 1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-ylcarbamat synthesis

Yield:103421-61-0 99%

Reaction Conditions:

with hydrogen bromide in acetic acid at 20; for 2 h;

Steps:

19

This compound (0.20 g, 0.50 mmol) was dissolved in 5.7 ml. of HBr (33% solution inAcOH) under N₂ and the solution was kept stirring at room temperature for 2 hr, then diluted with Et₂O (15 ml.) to obtain a suspension. The mixture was filtered and the solid dissolved in H₂O. The aqueous solution was then made alkaline with Na₂CO₃ and extracted with AcOEt. The organic phase was dried (Na₂SO₄), the solvent was removed under vacuum obtaining the title compound in 99% yield. M.p. 62-64 ⁰C.[¹H]-NMR (CD₃OD): 3.48 (s, 3H, Me); 4.43 (s, 1 H, CH); 7.26-7.32 (m, 2H), 7.39-7.46 (m, 2H), 7.47-7.54 (m, 1 H), 7.56-7.61 (m, 3H), 7.65-7.70 (m, 1 H) (aromatic protons) ppm.

References:

WO2009/81349,2009,A1 Location in patent:Page/Page column 21