Hydrazine hydrate (1:1) → 860653-06-1

HRID 1430670Notes

Reaction equation

HRID 1430670 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][C:12]([O:14]C)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:16][NH2:17].O>CO>[NH:16]([C:12](=[O:14])[CH2:11][CH2:10][CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[NH2:17]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 131123524-[[(1,1-dimethylethoxy)carbonyl]amino]Butanoic acid methyl ester

Product 1

HCID 57829537860653-06-1Yield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of methyl 4-(tert-butoxycarbonylamino)butanoate (21.0 g, 96.8 mmol) in MeOH (180 mL) was added NH2NH2.H2O (28.0 g, 483 mmol) at rt. The mixture was stirred at 65° C. for 12 hrs then concentrated under reduced pressure. The crude material was dissolved in DCM (400 mL). The organic layer was washed with water (2×), and saturated sodium chloride (2×), dried over Na2SO4, and concentrated to afford tert-butyl 4-hydrazinyl-4-oxobutylcarbamate (18.9 g, 90%) as a white solid. ESI-MS (EI+, m/z): 240 [M+Na]+.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. dissolutionThe crude material was dissolved in DCM (400 mL)
  3. washThe organic layer was washed with water (2×), and saturated sodium chloride (2×)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c8644d6e94f5465eacd376b0ff979b09
Source dataset
uspto-grants-2015_01
Patent number
US08940897B2

Reaction notes

Loading…