Hydrazine hydrate (1:1) → HCID 69686539, compound

Participants

Reaction Steps

A solution of (2-benzyl-6-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3,7-dioxo-[1,2]diazepan-1-yl]-acetic acid tert-butyl ester (5a) (150 mg, 0.31 mmol) and hydrazine monohydrate (17.3 mg, 35 mmol) in ethanol (1.5 mL) was stirred at room temperature for 6 hours. Solvent was removed in vacuo. The residue was taken up into acetic acid (1.5 mL) and stirred at room temperature for 30 min. The mixture was evaporated in vacuo and the resulting residue was dissolved in ethyl acetate (20 mL), washed with 5% Na2CO3 then water. The aqueous solution was extracted with ethyl acetate (20 mL×2). The combined organic layers were dried over Na2SO4 and filtered. The filtrate was evaporated to dryness in vacuo to afford 107 mg (98% yield) of the title compound. 1H-NMR (500 MHz, CDCl3) δ 1.45 (s, 9H), 1.70-1.78 (m, 1H), 2.30-2.48 (m, 2H), 3.10-3.15 (m 1H), 3.30-3.38 (m, 1H), 3.95-4.00 (d, 1H), 4.36-4.40 (d, 1H), 4.45-4.49 (d, 1H), 5.07-5.12 (d, 1H), 7.28-7.38 (m, 5H). Analytical HPLC: 8.03 min. LC-MS (ES+): m/e=348 (M+H+).

Provenance & Evidence