HCID 54255546, compound → HCID 54381947, compound

HRID 1706528Notes

Reaction equation

HRID 1706528 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[CH2:14][N:13]([CH:15]([C:30]([O:32][CH3:33])=[O:31])[C:16]3[CH:21]=[CH:20][C:19]([O:22]CC4C=CC=CC=4)=[CH:18][CH:17]=3)[C:12]2=[O:34])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>C(O)C.[Pd]>[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[CH2:14][N:13]([CH:15]([C:30]([O:32][CH3:33])=[O:31])[C:16]3[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=3)[C:12]2=[O:34])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 54255546HCID 54255546, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54381947HCID 54381947, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-(2-Phenylacetamido)-1-(α-methoxycarbonyl-4-benzyloxybenzyl)-2-azetidinone (70 mg) was dissolved in absolute ethanol (10 ml), and to the solution, there was added 10% palladium on carbon (30 mg). The mixture was subjected to catalytic reduction in a stream of hydrogen gas at ordinary temperature and ordinary atmospheric pressure. After a calculated volume of the hydrogen gas was absorbed into the mixture in the course of 3 hours, the catalyst was removed by filtration to give a filtrate, which was evaporated to dryness under reduced pressure. The resultant residue was treated with diethyl ether to give 3-(2-phenylacetamido)-1-(α-methoxycarbonyl-4-hydroxybenzyl)-2-azetidinone (40 mg), mp 171.5° to 175° C.

Workup

  1. customAfter a calculated volume of the hydrogen gas was absorbed into the mixture in the course of 3 hours
  2. customthe catalyst was removed by filtration
  3. customto give a filtrate, which
  4. customwas evaporated to dryness under reduced pressure
  5. additionThe resultant residue was treated with diethyl ether

Sources & evidence

ORD record
ord-0eaa4e8cf2314091bc7a487454fcb8fb
Source dataset
uspto-grants-1980_06
Patent number
US04207234

Reaction notes

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