Acetic Acid → HCID 68142324, compound

HRID 1729673Notes

Reaction equation

HRID 1729673 reaction equation
[Cl:1][C@@:2]1([CH3:34])[C@H:7]([C:8]([O:10]CC(Cl)(Cl)Cl)=[O:9])[N:6]2[C:16](=[O:33])[C@@H:17]([NH:18][C:19]([C:21]3[C:22]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[N:23][O:24][C:25]=3[CH3:26])=[O:20])[C@H:5]2[S:4][CH2:3]1.C(O)(=O)C>C(OCC)(=O)C.[Zn]>[Cl:1][C@@:2]1([CH3:34])[C@H:7]([C:8]([OH:10])=[O:9])[N:6]2[C:16](=[O:33])[C@@H:17]([NH:18][C:19]([C:21]3[C:22]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)=[N:23][O:24][C:25]=3[CH3:26])=[O:20])[C@H:5]2[S:4][CH2:3]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 68141103HCID 68141103, compound

Product 1

HCID 68142324HCID 68142324, compoundYield 55.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2,2,2-trichloroethyl 3β-chloro-3α-methyl-7β-(5-methyl-3-phenylisoxazol-4-carboxamido)cepham-4α-carboxylate (210 mg), zinc metal (250 mg), and acetic acid (3 ml) is stirred at room temperature for 3 hours. The reaction mixture is filtered to remove solid, and the filtrate is evaporated to give a residue, which is dissolved in ethyl acetate and washed with aqueous sodium hydrogen carbonate. The water layer is acidified with hydrochloric acid and extracted with ethyl acetate. The extract solution is washed with water, dried, and evaporated to give 3β-chloro-3α-methyl-7β-(5-methyl-3-phenylisoxazol-4-carboxamido)cepham-4α-carboxylic acid (89 mg). m.p. 210°C.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customto remove solid
  3. customthe filtrate is evaporated
  4. customto give a residue, which
  5. washwashed with aqueous sodium hydrogen carbonate
  6. extractionextracted with ethyl acetate
  7. washThe extract solution is washed with water
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-94601bccfc57458ba69b42d7aca93e29
Source dataset
uspto-grants-1976_11
Patent number
US03989685

Reaction notes

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