Acetic Acid → HCID 13362788, compound

HRID 1164569Notes

Reaction equation

HRID 1164569 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([NH:10][CH:11]2[C:31](=[O:32])[N:13]3[C:14]([C:18]([O:20]CC4C=CC([N+]([O-])=O)=CC=4)=[O:19])=[CH:15][CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.C(O)(=O)C.[H][H]>CO.O1CCCC1.[Pd]>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([NH:10][CH:11]2[C:31](=[O:32])[N:13]3[C:14]([C:18]([OH:20])=[O:19])=[CH:15][CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 88737397HCID 88737397, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13362788HCID 13362788, compoundYield 18.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-nitrobenzyl 7-[2-(2-amino-4-thiazolyl)acetamido]-3-cephem-4-carboxylate (1.4 g) in a mixture of methanol (25 ml) and tetrahydrofuran (60 ml) was added to a mixture of 10% palladium-on-carbon (1.7 g), glacial acetic acid (7 ml) and methanol (20 ml) in an atmosphere of nitrogen. Hydrogen gas was introduced into the mixture and shaken for 8.5 hours at room temperature. After removing the insoluble substance by filtration, the filtrate was concentrated under reduced pressure. The residue was pulverized with diethyl ether, and the resultant substance was dissolved in an aqueous solution of sodium bicarbonate, washed with ethyl acetate and diethyl ether in turn and then the remaining ether was removed by bubbling with nitrogen gas. The resultant solution was adjusted to pH 4.5 with dilute hydrochloric acid, subjected to column chromatography on macroporous non-ionic adsorption resin "Diaion HP-20" (Trademark, manufactured by Mitsubishi Chemical Industries Ltd.), and eluted with 20% isopropyl alcohol. Isopropyl alcohol was distilled off under reduced pressure and the remaining solution was lyophilized to give 7-[2-(2-amino-4-thiazolyl)acetamido]-3-cephem-4-carboxylic acid (185 mg).

Workup

  1. customAfter removing the insoluble substance
  2. filtrationby filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. dissolutionthe resultant substance was dissolved in an aqueous solution of sodium bicarbonate
  5. washwashed with ethyl acetate and diethyl ether in turn
  6. customthe remaining ether was removed
  7. customby bubbling with nitrogen gas
  8. wash" (Trademark, manufactured by Mitsubishi Chemical Industries Ltd.), and eluted with 20% isopropyl alcohol
  9. distillationIsopropyl alcohol was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e91dd1a3b9d34da3bb0dde9e3dee6f28
Source dataset
uspto-grants-1983_01
Patent number
US04370326

Reaction notes

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