HCID 131711547, compound → HCID 131711551, compound

HRID 971422Notes

Reaction equation

HRID 971422 reaction equation
[C:1]([CH:4]1[O:10][CH:9]2[C:6]([C:26](=[O:34])[CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)([C:7](=[O:25])[N:8]2[C:11](=[C:22]([CH3:24])[CH3:23])[C:12]([O:14]CC2C=CC=CC=2)=[O:13])[NH:5]1)(=[O:3])[CH3:2]>O1CCCC1.[C].[Pd]>[C:1]([CH:4]1[O:10][CH:9]2[C:6]([C:26](=[O:34])[CH2:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)([C:7](=[O:25])[N:8]2[C:11](=[C:22]([CH3:24])[CH3:23])[C:12]([OH:14])=[O:13])[NH:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 131711547HCID 131711547, compound

Product 1

HCID 131711551HCID 131711551, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 550 mg of benzyl α-(3ξ-acetyl-2-phenylacetyl-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-α-isopropylideneacetate in 8 ml of tetrahydrofuran is added 5% palladium carbon, and the mixture catalytically hydrogenated under atmospheric pressure for 2 hours. The insoluble material is removed by filtration, and the filtrate concentrated under reduced pressure. The residue (471 mg) is crystallized from a mixture of ether and petroleum ether to yield 421 mg of α-(3ξ-acetyl-2-phenylacetyl-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-α-isopropylideneacetic acid in 95% yield.

Workup

  1. customThe insoluble material is removed by filtration
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customThe residue (471 mg) is crystallized from a mixture of ether and petroleum ether

Sources & evidence

ORD record
ord-e4b099e0ea8247a5a9b21ae88fb3aed4
Source dataset
uspto-grants-1979_07
Patent number
US04159984

Reaction notes

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