Hydrazine hydrate (1:1) → tert-butyl N-[(hydrazinecarbonyl)methyl]carbamate

HRID 272297Notes

Reaction equation

HRID 272297 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([O:12]C)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[NH2:15][NH2:16]>>[NH:15]([C:10](=[O:12])[CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[NH2:16]

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 637609N-Boc-glycine methyl ester

Product 1

HCID 2735639tert-butyl N-[(hydrazinecarbonyl)methyl]carbamate

Procedure

To a stirred solution of methyl (tert-butyloxycarbonyl)glycinate (8.54 g, 45.1 mmol) was added hydrazine hydrate (4.4 mL, 90.5 mmol) and the reaction was heated under reflux for 16 hours. The solvent was removed in vacuo and the residue partitioned between dichloromethane (100 mL) and water (100 mL). The phases were separated, the aqueous phase evaporated in vacuo to low volume and extracted with 5% methanol/dichloromethane (2×100 mL) The organic extracts were combined, dried over magnesium sulfate and concentrated in vacuo to give the product as a white crystalline solid, 5.27 g (62%).

Workup

  1. temperaturethe reaction was heated
  2. temperatureunder reflux for 16 hours
  3. customThe solvent was removed in vacuo
  4. customthe residue partitioned between dichloromethane (100 mL) and water (100 mL)
  5. customThe phases were separated
  6. customthe aqueous phase evaporated in vacuo to low volume
  7. extractionextracted with 5% methanol/dichloromethane (2×100 mL) The organic extracts
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6cad0116a93643169fa517c01313d7c6
Source dataset
uspto-grants-2008_11
Patent number
US07456170B2

Reaction notes

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