HCID 23463637, compound → HCID 54250743, compound

HRID 1706531Notes

Reaction equation

HRID 1706531 reaction equation
C([O:8][C:9]([CH:11]([N:18]1[CH2:21][CH:20]([N:22]2[C:26](=[O:27])[C:25]3=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]3[C:23]2=[O:32])[C:19]1=[O:33])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:10])C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.[Pd]>[C:9]([CH:11]([N:18]1[CH2:21][CH:20]([N:22]2[C:23](=[O:32])[C:24]3=[CH:31][CH:30]=[CH:29][CH:28]=[C:25]3[C:26]2=[O:27])[C:19]1=[O:33])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([OH:10])=[O:8]

Participants

5

Reactant 2

HCID 23463637HCID 23463637, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54250743HCID 54250743, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1-(α-Benzyloxycarbonylbenzyl)-3-phthalimido-2-azetidinone (1.32 g) was dissolved in ethyl acetate (30 ml), and to the solution, there was added 10% palladium on carbon (500 mg), and 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 reaction mixture in the course of 3 hours. The reaction mixture was adjusted to about pH 8 with 2% aqueous sodium bicarbonate. The catalyst was removed by filtration from the reaction mixture and the aqueous layer was separated from the resultant filtrate. The aqueous solution was adjusted to pH 2 with 1 N hydrochloric acid and extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium chloride and then dried over magnesium sulfate. The solvent was removed by distillation from solution under reduced pressure to give an crystalline residue, which was washed with diethyl ether to give 1-(α-carboxybenzyl)-3-phthalimido-2-azetidinone (0.85 g), mp 182° to 183° C.

Workup

  1. customAfter a calculated volume of the hydrogen gas was absorbed into the reaction mixture in the course of 3 hours
  2. customThe catalyst was removed by filtration from the reaction mixture
  3. customthe aqueous layer was separated from the resultant filtrate
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with a saturated aqueous sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed by distillation from solution under reduced pressure
  8. customto give an crystalline residue, which
  9. washwas washed with diethyl ether

Sources & evidence

ORD record
ord-926a1b8071c34c0188c64375df53d128
Source dataset
uspto-grants-1980_06
Patent number
US04207234

Reaction notes

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