Methanol → HCID 178431946, compound

HRID 1448404Notes

Reaction equation

HRID 1448404 reaction equation
C(=O)(O)[O-].[K+].CO.[H][H].[O:10]([CH2:17][C:18]([NH:20][CH:21]1[C:41](=[O:42])[N:23]2[CH:24]([C:29]3[N:33](CC4C=CC=CC=4)[N:32]=[N:31][N:30]=3)[C:25]([CH3:28])([CH3:27])[S:26][C@H:22]12)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>[Pd].C(OCC)(=O)C.O>[O:10]([CH2:17][C:18]([NH:20][CH:21]1[C:41](=[O:42])[N:23]2[CH:24]([C:29]3[NH:33][N:32]=[N:31][N:30]=3)[C:25]([CH3:27])([CH3:28])[S:26][C@H:22]12)=[O:19])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 516893Potassium BicarbonateHCID 70604893HCID 70604893, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 178431946HCID 178431946, compoundYield 51%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 100 mg. (1 mmole) of potassium bicarbonate and 2.3 g. of 10% palladium-on-carbon, in a mixture of 12 ml. of methanol and 3 ml. of water, is stirred under an atmosphere of hydrogen until hydrogen uptake ceases. A solution of 464 mg. of 6-(2-phenoxyacetamido)-2,2-dimethyl-3-(1-benzyltetrazol-5-yl)penam in 10 ml. of ethyl acetate is then added, and stirring under an atmosphere of hydrogen is continued for an additional 5 hours. At this point the reaction mixture is filtered, and the residue is washed with aqueous methanol. The washings and the filtrate are combined and evaporated in vacuo. To this latter residue is added chloroform and water and the pH is adjusted to 8.0. The chloroform is removed and discarded, and fresh chloroform is added to the aqueous phase. The pH is lowered to 2.5 and the chloroform layer is separated. The dried chloroform is evaporated in vacuo, leaving 190 mg. (51% yield) of 6-(2-phenoxyacetamido)-2,2-dimethyl-3 -(5-tetrazolyl)penam.

Workup

  1. additionA mixture of 100 mg
  2. filtrationAt this point the reaction mixture is filtered
  3. washthe residue is washed with aqueous methanol
  4. customevaporated in vacuo
  5. additionTo this latter residue is added chloroform and water
  6. customThe chloroform is removed
  7. additionfresh chloroform is added to the aqueous phase
  8. customthe chloroform layer is separated
  9. customThe dried chloroform is evaporated in vacuo
  10. customleaving 190 mg

Sources & evidence

ORD record
ord-c2d379f9e3284cbfb52eee38ecf0a450
Source dataset
uspto-grants-1979_12
Patent number
US04179511

Reaction notes

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