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

HRID 272297

반응식

HRID 272297 반응식
[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]

참가 물질

3

반응물 2

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

생성물 1

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

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-6cad0116a93643169fa517c01313d7c6
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456170B2

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