Acetic Acid → HCID 86738684, compound

HRID 1902520Notes

Reaction equation

HRID 1902520 reaction equation
CO.C(O)(=O)C.[NH2:7][C:8]1[S:9][CH:10]=[C:11]([C:13](=[N:44][O:45][CH3:46])[C:14]([NH:16][CH:17]2[C:42](=[O:43])[N:19]3[CH:20]([C:29]([O:31]CC4C=CC([N+]([O-])=O)=CC=4)=[O:30])[C:21](=[CH:24][O:25][C:26](=[O:28])[CH3:27])[CH2:22][S:23][C@H:18]23)=[O:15])[N:12]=1.O>O1CCCC1.[C].[Pd]>[NH2:7][C:8]1[S:9][CH:10]=[C:11]([C:13](=[N:44][O:45][CH3:46])[C:14]([NH:16][CH:17]2[C:42](=[O:43])[N:19]3[CH:20]([C:29]([OH:31])=[O:30])[C:21](=[CH:24][O:25][C:26](=[O:28])[CH3:27])[CH2:22][S:23][C@H:18]23)=[O:15])[N:12]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 962WaterHCID 86738683HCID 86738683, compound

Product 1

HCID 86738684HCID 86738684, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Methanol (10 ml) and acetic acid (3 ml.) were added to a solution of 4-nitrobenzyl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-acetoxymethylenecepham-4-carboxylate (syn isomer, 2.5 g.) in tetrahydrofuran (60 ml.). 10% palladium-carbon (0.5 g.) containing water (2 ml.) was added to a solution and the mixture was subjected to catalytic reduction under ordinary pressure for 3 hours. After removing the insoluble substance from the resultant mixture by filtration, the filtrate was concentrated under reduced pressure. Ethyl acetate and an aqueous solution of sodium bicarbonate were added to the solution and adjusted to pH 7.5. The insoluble substance was removed from the mixture. The aqueous layer was separated, adjusted to pH 5.0 and washed with ethyl acetate. The solution was adjusted to pH 3.0 and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and treated with activated charcoal. After concentrating the solution under reduced pressure, the residue was pulverized with diisopropyl ether and collected by filtration to give 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-acetoxymethylenecepham-4-carboxylic acid (syn isomer, 0.27 g.).

Workup

  1. additionwas added to a solution
  2. customAfter removing the insoluble substance from the resultant mixture
  3. filtrationby filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionEthyl acetate and an aqueous solution of sodium bicarbonate were added to the solution
  6. customThe insoluble substance was removed from the mixture
  7. customThe aqueous layer was separated
  8. washwashed with ethyl acetate
  9. extractionextracted with ethyl acetate
  10. washThe extract was washed with a saturated aqueous solution of sodium chloride
  11. dry with materialdried over magnesium sulfate
  12. additiontreated with activated charcoal
  13. concentrationAfter concentrating the solution under reduced pressure
  14. filtrationcollected by filtration

Sources & evidence

ORD record
ord-f83b9e5599eb4c20b685c9a61073e7d6
Source dataset
uspto-grants-1982_12
Patent number
US04363807

Reaction notes

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