Methanol → HCID 131712225, compound

HRID 1075235Notes

Reaction equation

HRID 1075235 reaction equation
[CH:1]([NH:3][C:4]1[N:9]=[C:8]([C:10](=[N:37][O:38][CH3:39])[C:11]([NH:13][CH:14]2[C:35](=[O:36])[N:16]3[C:17]([C:22]([O:24]CC4C=CC([N+]([O-])=O)=CC=4)=[O:23])=[C:18]([Cl:21])[CH2:19][S:20][C@H:15]23)=[O:12])[CH:7]=[CH:6][CH:5]=1)=[O:2].CO>[Pd].O1CCCC1>[CH:1]([NH:3][C:4]1[N:9]=[C:8]([C:10](=[N:37][O:38][CH3:39])[C:11]([NH:13][CH:14]2[C:35](=[O:36])[N:16]3[C:17]([C:22]([OH:24])=[O:23])=[C:18]([Cl:21])[CH2:19][S:20][C@H:15]23)=[O:12])[CH:7]=[CH:6][CH:5]=1)=[O:2]

Participants

5

Reactant 2

HCID 887MethanolHCID 131712226HCID 131712226, compound

Product 1

HCID 131712225HCID 131712225, compoundYield 62.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-nitrobenzyl 7-[2-(6-formamidopyridin-2-yl)-2-methoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate (syn isomer) (1.43 g.), 10% palladium on carbon (0.8 g.), methanol (30 ml.) and tetrahydrofuran (60 ml.) was subjected to catalytic reduction at ambient temperature under ordinary pressure for 4 hours. After removing the catalyst by filtration, the filtrate was concentrated under reduced pressure. An aqueous solution of sodium bicarbonate and ethyl acetate were added to the residue, and the aqueous layer was separated. The aqueous layer was adjusted to pH 6, washed with ethyl acetate, and then adjusted to pH 1 to 2. The aqueous layer was extracted with ethyl acetate. The ethyl acetate extract was washed with an aqueous solution of sodium chloride, dried over magnesium sulfate, and concentrated under reduced pressure. Diethyl ether (30 ml.) was added to the residue, stirred for one hour, and then precipitates were collected by filtration to give 7-[2-(6-formamidopyridin-2-yl)-2-methoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylic acid (syn isomer) (680 mg.), brownish yellow powder, mp. 200° to 204° C. (dec.).

Workup

  1. customAfter removing the catalyst
  2. filtrationby filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionAn aqueous solution of sodium bicarbonate and ethyl acetate were added to the residue
  5. customthe aqueous layer was separated
  6. washwashed with ethyl acetate
  7. extractionThe aqueous layer was extracted with ethyl acetate
  8. extractionThe ethyl acetate extract
  9. washwas washed with an aqueous solution of sodium chloride
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. additionDiethyl ether (30 ml.) was added to the residue
  13. customprecipitates
  14. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-4510b458493441acbdcae72fe334c995
Source dataset
uspto-grants-1983_07
Patent number
US04395411

Reaction notes

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