Hydrazine hydrate (1:1) → HCID 86701020, compound

HRID 1427645Notes

Reaction equation

HRID 1427645 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:15])[CH2:9][CH2:10][C:11](OC)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[NH2:17][NH2:18]>CCO>[NH:17]([C:11](=[O:12])[CH2:10][CH2:9][N:8]([CH3:15])[C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[NH2:18]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 10703983HCID 10703983, compound

Product 1

HCID 86701020HCID 86701020, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 3-(tert-butoxycarbonyl(methyl)amino)propanoate (6.9 g, 0.0317 mol) in EtOH (15 mL) was added hydrazine monohydrate (7.7 mL, 0.158 mol) at rt. The reaction mixture was heated to 80° C. and stirred at 80° C. overnight. The reaction mixture was concentrated, and then DCM (300 mL) was added. The organic layer was washed with water and saturated sodium chloride, dried over Na2SO4, and concentrated to afford tert-butyl 3-hydrazinyl-3-oxopropyl(methyl)carbamate (6.8 g, 98%) as sticky oil, which was used directly in the next step. ESI-MS (EI+, m/z): 118 [M−100+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionDCM (300 mL) was added
  3. washThe organic layer was washed with water and saturated sodium chloride
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-723cb93970ea4df2895ed56f6fb67a51
Source dataset
uspto-grants-2015_01
Patent number
US08933233B2

Reaction notes

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