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

HRID 1855179Notes

Reaction equation

HRID 1855179 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 concenreated 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

Sources & evidence

ORD record
ord-80284cb785eb458a955e4cacc98c3773
Source dataset
uspto-grants-2015_02
Patent number
US08962843B2

Reaction notes

Loading…