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

HRID 400459
Notes
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Reaction equation

HRID 400459 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].[CH3:24][NH:25][NH2:26]>C1COCC1.O>[C:5]([O:9][C:10]([N:12]1[CH2:18][CH2:17][C:16]2=[N:26][N:25]([CH3:24])[C:21](=[O:23])[CH2:20][CH:15]2[CH2:14][CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 6061MethylhydrazineHCID 834890002-(1-Tert-butoxycarbonyl-5-oxo-azepan-4-YL)acetic acid

Product 1

HCID 866860582-Methyl-3-oxo-2,3,4,4a,5,6,8,9-octahydro-1,2,7-triaza-benzocycloheptene-7-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 8028
Tetrahydrofuran
Solvent

Procedure

36 mL acetic acid was added to 10.5 g 4-carboxymethyl-5-oxo-azepane-1-carboxylic acid tert-butyl ester in 75 mL THF at 5° C. 3.1 mL methylhydrazine was added to the mixture and refluxed for 3 h. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine. The crude product was purified by column chromatography on silica gel to yield 6.9 g of the desired product. (M+H)+: 282

Workup

  1. temperaturerefluxed for 3 h
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-9aead832d4484b8aaaafd492b11402f1
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08741892B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes