Hydrazine hydrate (1:1) → HCID 86701057, compound

HRID 1855606Notes

Reaction equation

HRID 1855606 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:12][CH:11]([CH2:13][C:14]([O:16]CC)=O)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[NH2:20][NH2:21]>CCO>[NH:20]([C:14](=[O:16])[CH2:13][CH:11]1[CH2:12][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:10]1)[NH2:21]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86701059Cyclobutaneacetic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-, ethyl ester

Product 1

HCID 86701057HCID 86701057, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 2-(3-(tert-butoxycarbonylamino)cyclobutyl)acetate (1.2 g, 4.7 mmol) and hydrazine hydrate (1.4 g, 23.5 mmol) in EtOH (8 mL) was heated at 80° C. for 17 hrs. The reaction mixture was concentrated and the residue was dissolved in DCM (20 mL). The organic phase was washed with saturated sodium chloride (10 mL) and water (10 mL). The water layer was exacted with EtOAc (3×). The combined organic layer was dried over Na2SO4 and concentrated to afford tert-butyl 3-(2-hydrazinyl-2-oxoethyl)cyclobutylcarbamate (1.1 g, 97%). ESI-MS (EI+, m/z): 244 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in DCM (20 mL)
  3. washThe organic phase was washed with saturated sodium chloride (10 mL) and water (10 mL)
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2a42f8e28bc84e5ca15b7903eafe4619
Source dataset
uspto-grants-2015_02
Patent number
US08962844B2

Reaction notes

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