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

HRID 2231074Notes

Reaction equation

HRID 2231074 reaction equation
[C:1]([O:5][C:6](=[O:35])[CH2:7][N:8]1[C:14](=[O:15])[CH:13]([N:16]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:12][CH2:11][C:10](=[O:27])[N:9]1[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([CH3:4])([CH3:3])[CH3:2].O.NN>C(O)C>[C:1]([O:5][C:6](=[O:35])[CH2:7][N:8]1[C:14](=[O:15])[CH:13]([NH2:16])[CH2:12][CH2:11][C:10](=[O:27])[N:9]1[CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 54408335HCID 54408335, compound

Product 1

HCID 69686539HCID 69686539, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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+).

Workup

  1. customSolvent was removed in vacuo
  2. customThe mixture was evaporated in vacuo
  3. dissolutionthe resulting residue was dissolved in ethyl acetate (20 mL)
  4. washwashed with 5% Na2CO3
  5. extractionThe aqueous solution was extracted with ethyl acetate (20 mL×2)
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. customThe filtrate was evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-597341a27e334d5cb940b22e01509b99
Source dataset
uspto-grants-2002_07
Patent number
US06426413B1

Reaction notes

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