7-(2-Methoxyimino-3,3-ethylenedioxybutyramido)-3-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid → 7-(2-Methoxyimino-3,3-ethylenedioxybutyramido)-3-methylenecepham-4-carboxylic acid

HRID 1982036Notes

Reaction equation

HRID 1982036 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:28]1([O:33][CH2:32][CH2:31][O:30]1)[CH3:29])[C:5]([NH:7][CH:8]1[C:26](=[O:27])[N:10]2[C:11]([C:23]([OH:25])=[O:24])=[C:12]([CH2:15]SC3SC(C)=NN=3)[CH2:13][S:14][C@H:9]12)=[O:6]>O1CCCC1.O.C(O)(=O)C.[Zn]>[CH3:1][O:2][N:3]=[C:4]([C:28]1([O:33][CH2:32][CH2:31][O:30]1)[CH3:29])[C:5]([NH:7][CH:8]1[C:26](=[O:27])[N:10]2[CH:11]([C:23]([OH:25])=[O:24])[C:12](=[CH2:15])[CH2:13][S:14][C@H:9]12)=[O:6]

Participants

6

Reactant 1

HCID 1317125297-(2-Methoxyimino-3,3-ethylenedioxybutyramido)-3-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid

Product 1

HCID 1317125257-(2-Methoxyimino-3,3-ethylenedioxybutyramido)-3-methylenecepham-4-carboxylic acidYield 42.8%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Zinc powder (500 mg.) and copper sulfate 5-hydrate (50 mg.) were added to a solution of 7-(2-methoxyimino-3,3-ethylenedioxybutyramido)-3-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 500 mg.) in tetrahydrofuran (6 ml.), water (2 ml.) and acetic acid (1 ml.), and stirred at room temperature for 2 hours. The resultant mixture was filtered and washed with tetrahydrofuran (5 ml.). The filtrate and the washings were combined and treated in a similar manner to that of Example 10-(3) to give a mixture (160 mg.) of 7-(2-methoxyimino-3,3-ethylenedioxybutyramido)-3-methylenecepham-4-carboxylic acid (syn isomer) and 7-(2-methoxyimino-3,3-ethylenedioxybutyramido)-3-methyl-3-cephem-4-carboxylic acid (syn isomer).

Workup

  1. filtrationThe resultant mixture was filtered
  2. washwashed with tetrahydrofuran (5 ml.)
  3. additiontreated in a similar manner to that of Example 10-(3)

Sources & evidence

ORD record
ord-3dc2fb72e6894d9981833a94b90268fc
Source dataset
uspto-grants-1986_06
Patent number
US04594446

Reaction notes

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