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3-Azido-4-(3-benzyloxycarbonyl-3-diazo-2-oxopropyl)-azetidin-2-one → Benzyl 6-azido-1-azabicyclo[3.2.0]-heptan-3,7-dione-2-carboxylate

HRID 1154918
Notes
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Reaction equation

HRID 1154918 reaction equation
[N:1]([CH:4]1[CH:7]([CH2:8][C:9](=[O:23])[C:10]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])=[N+]=[N-])[NH:6][C:5]1=[O:24])=[N+:2]=[N-:3]>C1C=CC=CC=1.C([O-])(=O)C.[Rh+3].C([O-])(=O)C.C([O-])(=O)C>[N:1]([CH:4]1[C:5](=[O:24])[N:6]2[CH:7]1[CH2:8][C:9](=[O:23])[CH:10]2[C:13]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:14])=[N+:2]=[N-:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 545275133-Azido-4-(3-benzyloxycarbonyl-3-diazo-2-oxopropyl)-azetidin-2-one

Product 1

HCID 20563654Benzyl 6-azido-1-azabicyclo[3.2.0]-heptan-3,7-dione-2-carboxylate

Reagents, catalysts & solvents 2

HCID 168478Rhodium acetateCatalystHCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of rhodium acetate (2 mg) and 3-azido-4-(3-benzyloxycarbonyl-3-diazo-2-oxopropyl)azetidin-2-one (1 mmol) in anhydrous benzene (20 ml) is deoxygenated by bubbling nitrogen through it for 15 mins. The suspension is then stirred with heating in an oil bath at 80° C. for 30 min. After cooling to room temperature, the mixture is filtered and the filtrate is evaporated under vacuum to provide benzyl 6-azido-1-azabicyclo[3.2.0]-heptan-3,7-dione-2-carboxylate.

Workup

  1. customis deoxygenated
  2. customby bubbling nitrogen through it for 15 mins
  3. temperatureAfter cooling to room temperature
  4. filtrationthe mixture is filtered
  5. customthe filtrate is evaporated under vacuum

Sources & evidence

ORD record
ord-e329eb5694db413da2340847347c172c
Source dataset
uspto-grants-1981_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04298741

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes