HCID 12552203, compound → HCID 20332218, compound

HRID 2057431Notes

Reaction equation

HRID 2057431 reaction equation
[O:1]=[C:2]1[N:8]2[CH:4]([CH2:5][C:6]([S:19][C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][CH:21]=3)=[C:7]2[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:3]1>[Pd].C(O)C>[O:1]=[C:2]1[N:8]2[CH:4]([CH2:5][C:6]([S:19][C:20]3[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=3)=[C:7]2[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:3]1

Participants

4

Reactant 1

HCID 12552203HCID 12552203, compound

Product 1

HCID 20332218HCID 20332218, compoundYield 75.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A catalyst of 10% palladium on charcoal (Engelhard 4505, 50 mg) suspended in 90% aqueous ethanol (10 ml) was prehydrogenated for 20 minutes at room temperature/atmospheric pressure. Benzyl 7-oxo-3-p-nitrophenylthio-1-azabicyclo [3.2.0]hept-2-ene-2-carboxylate (50 mg) partially dissolved in ethanol (10 ml) was added, and the mixture was hydrogenated at room temperature and atmospheric pressure for 1.5 hours. The catalyst was removed by filtration through "High-Flo", and the colourless filtrate was evaporated to give an oil (35 mg) identical by TLC, u.v. and I.R. to the product (22) obtained in Example 7.

Workup

  1. additionwas added
  2. customwas hydrogenated at room temperature
  3. waitatmospheric pressure for 1.5 hours
  4. customThe catalyst was removed by filtration through "High-Flo"
  5. customthe colourless filtrate was evaporated

Sources & evidence

ORD record
ord-9fd4ae94c1524a4d99b4af63061147a0
Source dataset
uspto-grants-1980_07
Patent number
US04210661

Reaction notes

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