Acetic Acid → 7-[2-(2-Amino-4-thiazolyl)-2-isopropoxyiminoacetamido]-3-cephem-4-carboxylic acid

HRID 544012Notes

Reaction equation

HRID 544012 reaction equation
C(O)(=O)C.[NH2:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:37][O:38][CH:39]([CH3:41])[CH3:40])[C:12]([NH:14][CH:15]2[C:35](=[O:36])[N:17]3[C:18]([C:22]([O:24]CC4C=CC([N+]([O-])=O)=CC=4)=[O:23])=[CH:19][CH2:20][S:21][C@H:16]23)=[O:13])[N:10]=1.Cl>[Pd].O.O1CCCC1>[NH2:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:37][O:38][CH:39]([CH3:41])[CH3:40])[C:12]([NH:14][CH:15]2[C:35](=[O:36])[N:17]3[C:18]([C:22]([OH:24])=[O:23])=[CH:19][CH2:20][S:21][C@H:16]23)=[O:13])[N:10]=1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 1317124544-Nitrobenzyl 7-[2-(2-amino-4-thiazolyl)-2-isopropoxyiminoacetamido]-3-cephem-4-carboxylate

Product 1

HCID 1317135047-[2-(2-Amino-4-thiazolyl)-2-isopropoxyiminoacetamido]-3-cephem-4-carboxylic acidYield 21.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Acetic acid (1 ml.) and a suspension of 10% palladium on carbon (2.0 g.) in water (8 ml) were added to a solution of 4-nitrobenzyl 7-[2-(2-amino-4-thiazolyl)-2-isopropoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 5.0 g.) in tetrahydrofuran (150 ml.), and the suspension was subjected to catalytic reduction at room temperature under ordinary pressure. After removing the catalyst by filtration, the filtrate was concentrated under reduced pressure. Ethylacetate (80 ml.) was added to the residue, and adjusted to pH 7.5 with an aqueous solution of sodium bicarbonate. The organic layer was separated and extracted with an aqueous solution of sodium bicarbonate. The extract and the aqueous layer obtained above were combined, adjusted to pH 3.0 with conc. hydrochloric acid and extracted with tetrahydrofuran. The extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure. The precipitating crystalls were collected by filtration and dried to give 7-[2-(2-amino-4-thiazolyl)-2 -isopropoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 0.8 g.).

Workup

  1. customwas subjected to catalytic reduction at room temperature under ordinary pressure
  2. customAfter removing the catalyst
  3. filtrationby filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionEthylacetate (80 ml.) was added to the residue
  6. customThe organic layer was separated
  7. extractionextracted with an aqueous solution of sodium bicarbonate
  8. extractionThe extract
  9. customthe aqueous layer obtained above
  10. extractionextracted with tetrahydrofuran
  11. washThe extract was washed with a saturated aqueous solution of sodium chloride
  12. dry with materialdried over magnesium sulfate
  13. concentrationconcentrated under reduced pressure
  14. filtrationThe precipitating crystalls were collected by filtration
  15. customdried

Sources & evidence

ORD record
ord-48693939af1e40a6aaae6da81aaafe55
Source dataset
uspto-grants-1984_05
Patent number
US04447430

Reaction notes

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