p-Nitrobenzyl 7-{2-(1,2,3-thiadiazol-4-yl)-2-methoxyiminoacetamido}-3-cephem-4-carboxylate → 7-{2-(1,2,3-Thiadiazol-4-yl)-2-methoxyiminoacetamido}-3-cephem-4-carboxylic acid

HRID 621289Notes

Reaction equation

HRID 621289 reaction equation
[S:1]1[CH:5]=[C:4]([C:6](=[N:32][O:33][CH3:34])[C:7]([NH:9][CH:10]2[C:30](=[O:31])[N:12]3[C:13]([C:17]([O:19]CC4C=CC([N+]([O-])=O)=CC=4)=[O:18])=[CH:14][CH2:15][S:16][C@H:11]23)=[O:8])[N:3]=[N:2]1>CO.O1CCCC1.[C].[Pd]>[S:1]1[CH:5]=[C:4]([C:6](=[N:32][O:33][CH3:34])[C:7]([NH:9][CH:10]2[C:30](=[O:31])[N:12]3[C:13]([C:17]([OH:19])=[O:18])=[CH:14][CH2:15][S:16][C@H:11]23)=[O:8])[N:3]=[N:2]1

Participants

5

Reactant 1

HCID 131712449p-Nitrobenzyl 7-{2-(1,2,3-thiadiazol-4-yl)-2-methoxyiminoacetamido}-3-cephem-4-carboxylate

Product 1

HCID 1317130197-{2-(1,2,3-Thiadiazol-4-yl)-2-methoxyiminoacetamido}-3-cephem-4-carboxylic acidYield 24.8%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

10% Palladium carbon (0.85 g.) was added to a solution of p-nitrobenzyl 7-{2-(1,2,3-thiadiazol-4-yl)-2-methoxyiminoacetamido}-3-cephem-4-carboxylate (syn isomer, 1.65 g.) in methanol (70 ml.) and tetrahydrofuran (90 ml.), and the mixture was subjected to catalytic reduction at room temperature under atmospheric pressure for 3.5 hours. After removing the catalyst from the reaction mixtue by filtration, the filtrate was concentrated under reduced pressure. Water was added to the residue, and the mixture was adjusted to pH 7 to 8 with sodium bicarbonate, washed with ethyl acetate, adjusted to pH 1.5 with 10% hydrochloric acid, and then extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure, and the residue was pulverized with diethyl ether. The precipitates were collected by filtration and the dried to give yellow powder of 7-{2-(1,2,3-thiadiazol-4-yl)-2-methoxyiminoacetamido}-3 -cephem-4-carboxylic acid (syn isomer, 0.3 g.), m.p. 200° to 210° C. (dec.).

Workup

  1. customAfter removing the catalyst from the reaction mixtue
  2. filtrationby filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionWater was added to the residue
  5. washwashed with ethyl acetate
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure
  11. filtrationThe precipitates were collected by filtration
  12. customthe dried

Sources & evidence

ORD record
ord-c30185405def4224b36cd3f1cf430212
Source dataset
uspto-grants-1989_04
Patent number
US04822888

Reaction notes

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