Acetic Acid → 3-Oxo-2,3,4,4a, 5,6,8,9-octahydro-1,2,7-triaza-benzocycloheptene-7-carboxylic acid tert-butyl ester

HRID 400456Notes

Reaction equation

HRID 400456 reaction equation
C(O)(=O)C.[C:5]([O:9][C:10]([N:12]1[CH2:18][CH2:17][C:16](=O)[CH:15]([CH2:20][C:21]([OH:23])=O)[CH2:14][CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6].O.[NH2:25][NH2:26]>C1COCC1>[C:5]([O:9][C:10]([N:12]1[CH2:18][CH2:17][C:16]2=[N:25][NH:26][C:21](=[O:23])[CH2:20][CH:15]2[CH2:14][CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 834890002-(1-Tert-butoxycarbonyl-5-oxo-azepan-4-YL)acetic acid

Product 1

HCID 866865123-Oxo-2,3,4,4a, 5,6,8,9-octahydro-1,2,7-triaza-benzocycloheptene-7-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

60 mL acetic acid was added to 16 g 4-carboxymethyl-5-oxo-azepane-1-carboxylic acid tert-butyl ester in 120 mL THF at 5° C. 14 mL hydrazine hydrate was added to the reaction and the mixture was refluxed over night. After completion of the reaction, volatiles were removed and the residue was basified with sodium carbonate and extracted with chloroform. The organic layer was dried and concentrated under reduced pressure to afford 11 g of the desired product

Workup

  1. temperaturethe mixture was refluxed over night
  2. customAfter completion of the reaction, volatiles
  3. customwere removed
  4. extractionextracted with chloroform
  5. customThe organic layer was dried
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f45dff4a0e1d4ebeb7027b0a74857ca5
Source dataset
uspto-grants-2014_06
Patent number
US08741892B2

Reaction notes

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