2-Azetidinone → HCID 70606043, compound

HRID 2163286Notes

Reaction equation

HRID 2163286 reaction equation
N1CCC1=O.[C:6]([O:10][C:11]([C:13]([N:18]1[CH:21]([S:22]C=O)[CH:20]([NH:25][C:26](=[O:35])[CH2:27][O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:19]1=[O:36])=[C:14]([OH:17])[CH2:15]Br)=[O:12])([CH3:9])([CH3:8])[CH3:7]>ClCCl>[O:28]([CH2:27][C:26]([NH:25][CH:20]1[C:19](=[O:36])[N:18]2[C:13]([C:11]([O:10][C:6]([CH3:8])([CH3:7])[CH3:9])=[O:12])=[C:14]([OH:17])[CH2:15][S:22][C@H:21]12)=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 1367212-Azetidinone2×HCID 76211239HCID 76211239, compound

Product 1

HCID 70606043HCID 70606043, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The azetidin-2-ones provided by this invention are useful as intermediates in the preparation of 3-hyroxy cephalosporin antibiotics. In particular, a 1-(1-protectedcarboxy-2-hydroxy-3-bromo-1-propenyl)-3-amido(or imido)-4-formylthio-azetidin-2-one of this invention can readily be cyclized to provide the corresponding 7-amido (or imido)-4-protected-carboxy-3-hydroxy-3-cephem. Such cyclization of the azetidinone is effected by reaction with a cyclizing agent, such as for example 1,5-diazobicyclo[5.4.0]undec-5-ene (DBU) or mercuric acetate. As an example, 1-(1-tert.-butyloxycarbonyl-2-hydroxy-3-bromo-1-propenyl)-3-phenoxyacetamido-4-formylthio-azetidin-2-one can be treated with DBU in a suitable solvent, for instance dichloromethane, thereby effecting a cyclization of the azetidinone to provide tert.-butyl 7-phenoxyacetamido- 3-hydroxy-3-cephem-4-carboxylate.

Sources & evidence

ORD record
ord-90498e96b1504b989f7e477dc801eaa5
Source dataset
uspto-grants-1979_01
Patent number
US04133808

Reaction notes

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