Acetic Acid → HCID 178436978, compound

HRID 2351148Notes

Reaction equation

HRID 2351148 reaction equation
[C:1](/[CH:3]=[CH:4]\[S:5][CH2:6][C:7]([NH:9][CH:10]1[C:32](=[O:33])[N:12]2[C:13]([C:19]([O:21]CC3C=CC([N+]([O-])=O)=CC=3)=[S:20])=[C:14]([CH:17]=[CH2:18])[CH2:15][S:16][C@H:11]12)=[O:8])#[N:2].CO.C(O)(=O)C.[H][H]>[Pd].O1CCCC1>[C:1](/[CH:3]=[CH:4]\[S:5][CH2:6][C:7]([NH:9][CH:10]1[C:32](=[O:33])[N:12]2[C:13]([C:19]([OH:21])=[S:20])=[C:14]([CH:17]=[CH2:18])[CH2:15][S:16][C@H:11]12)=[O:8])#[N:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 131716164HCID 131716164, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 178436978HCID 178436978, compoundYield 44.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

p-Nitrobenzyl 7-[2-((Z)-2-cyanovinylthio)-acetamido]-3-vinylthio-3-cephem-4-carboxylate (300 mg) was hydrogenated in the presence of 10% palladium on carbon (270 mg) in a mixture of tetrahydrofuran (9 ml), methanol (1.5 ml) and acetic acid (0.033 ml) at ambient temperature for 3 hours under 1 atmospheric pressure of hydrogen. The catalyst was filtered off and washed with methanol. The filtrate and washings were combined and concentrated in vacuo. The residue was dissolved in a mixture of ethyl acetate and water at pH 7. The aqueous layer was separated, adjusted to pH 7 with dilute hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, concentrated in vacuo and triturated with diisopropyl ether to give 7-[2-((Z)-2-cyanovinylthio)acetamido]-3-vinylthio-3-cephem-4-carboxylic acid (97 mg).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with methanol
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in a mixture of ethyl acetate and water at pH 7
  5. customThe aqueous layer was separated
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customtriturated with diisopropyl ether

Sources & evidence

ORD record
ord-4804fa3103b44162b61950c78d893b30
Source dataset
uspto-grants-1989_10
Patent number
US04871730

Reaction notes

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