1,4-Cyclohexadiene → (3S-trans)-3-[(2,6-Dimethoxybenzoyl)amino]-1-hydroxy-4-methyl-2-azetidinone

HRID 484682Notes

Reaction equation

HRID 484682 reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[C:4]=1[C:5]([NH:7][C@H:8]1[C@H:11]([CH3:12])[N:10]([O:13]CC2C=CC=CC=2)[C:9]1=[O:21])=[O:6].C1CC=CCC=1>C(O)C.[Pd]>[CH3:27][O:26][C:22]1[CH:23]=[CH:24][CH:25]=[C:3]([O:2][CH3:1])[C:4]=1[C:5]([NH:7][C@H:8]1[C@H:11]([CH3:12])[N:10]([OH:13])[C:9]1=[O:21])=[O:6]

Participants

5

Reactant 2

HCID 123431,4-CyclohexadieneHCID 13036849(3S-trans)-3-[(2,6-dimethoxybenzoyl)amino]-4-methyl-1-[(phenylmethyl)oxy]-2-azetidinone

Product 1

HCID 13036851(3S-trans)-3-[(2,6-Dimethoxybenzoyl)amino]-1-hydroxy-4-methyl-2-azetidinone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of (3S-trans)-3-[(2,6-dimethoxybenzoyl)amino]-4-methyl-1-[(phenylmethyl)oxy]-2-azetidinone (0.848 g) in absolute ethanol (20 ml) under nitrogen is added 1,4-cyclohexadiene (8 ml) and freshly prepared palladium black (approximately 0.85 g). After one hour the reaction mixture is filtered and evaporated to a solid (0.605 g).

Workup

  1. filtrationAfter one hour the reaction mixture is filtered
  2. customevaporated to a solid (0.605 g)

Sources & evidence

ORD record
ord-f11ae1338b2c42aaab4c9629d7f790f8
Source dataset
uspto-grants-1985_08
Patent number
US04533660

Reaction notes

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