HCID 56634376, compound → HCID 18640037, compound

HRID 464565Notes

Reaction equation

HRID 464565 reaction equation
[CH3:1][C:2]([CH3:26])([O:4][C:5]([NH:7][C@H:8]1[C@H:11]([CH3:12])[N:10]([O:13][CH2:14][C:15]([O:17]CC2C=CC=CC=2)=[O:16])[C:9]1=[O:25])=[O:6])[CH3:3]>C(O)C.[Pd]>[CH3:26][C:2]([CH3:1])([O:4][C:5]([NH:7][C@H:8]1[C@H:11]([CH3:12])[N:10]([O:13][CH2:14][C:15]([OH:17])=[O:16])[C:9]1=[O:25])=[O:6])[CH3:3]

Participants

4

Reactant 1

HCID 56634376HCID 56634376, compound

Product 1

HCID 18640037HCID 18640037, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(3S-trans)-3-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-methyl-1-[[(phenylmethoxy)carbonyl]methoxy]-2-azetidinone (0.73 g, 2.0 mmol) was dissolved in 12 ml of absolute ethanol and 0.36 g of 10% palladium on charcoal was added under argon. Hydrogenolysis (1 atmosphere, 20° C.) was completed in 30 minutes. The reaction mixture was filtered and the volatiles were removed to yield 0.55 g of crude (3S-trans)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-methyl-1-(carboxymethoxy)-2-azetidinone.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe volatiles were removed

Sources & evidence

ORD record
ord-879bb3f9f8c54a8da869cf6a46557471
Source dataset
uspto-grants-1985_10
Patent number
US04548747

Reaction notes

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