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 1856071Notes

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]

Participants

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

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

Sources & evidence

ORD record: ord-2ba88a5e8ac34d6f82ad2666c562898d
Source dataset: uspto-grants-1980_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04217453

Reaction notes

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