Pyridine → Benzhydryl 7-amino-3-cephem-4-carboxylate

HRID 1657424Notes

Reaction equation

HRID 1657424 reaction equation
S1C=CC=C1CC([NH:9][CH:10]1[C:33](=[O:34])[N:12]2[C:13]([C:17]([O:19][CH:20]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])=[CH:14][CH2:15][S:16][C@H:11]12)=O.N1C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl>[H-].[Ca+2].[H-]>[NH2:9][CH:10]1[C:33](=[O:34])[N:12]2[C:13]([C:17]([O:19][CH:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:18])=[CH:14][CH2:15][S:16][C@H:11]12

Participants

5

Reactant 3

HCID 1049PyridineHCID 24819Phosphorus pentachlorideHCID 70617022HCID 70617022, compound

Product 1

HCID 12098365Benzhydryl 7-amino-3-cephem-4-carboxylate

Reagents, catalysts & solvents 1

HCID 3033859Calcium hydrideSolvent

Procedure

Benzhydryl 7-(2-thienylacetamido)-3-cephem-4-carboxylate (2.45 g. 5 mmol) was dissolved in calcium hydride dried benzene (130 ml) containing dry pyridine (0.59 g, 7.4 mmol). The solution was maintained at 0° and PCl5 (1.54 g. 7.4 mmol.) was added with stirring. The reaction mixture was stirred under nitrogen at 0° for 3 hours and then the solvent was removed in vacuo. Anhydrous methanol (260 ml) was added to the residue and the resultant mixture was allowed to stand 2 hours. The methanol was removed in vacuo and the residue was treated with 20% aqueous tetrahydrofuran. After 15 minutes the tetrahydrofuran was removed in vacuo and the aqueous residue was adjusted to pH 7.5 and extracted with ethyl acetate. The extracts were washed with water, dried over MgSO4 and evaporated to give the solid product which was triturated with chloroform-petroleum ether and dried under high vacuum.

Workup

  1. temperatureThe solution was maintained at 0°
  2. stirringThe reaction mixture was stirred under nitrogen at 0° for 3 hours
  3. customthe solvent was removed in vacuo
  4. additionAnhydrous methanol (260 ml) was added to the residue
  5. customThe methanol was removed in vacuo
  6. additionthe residue was treated with 20% aqueous tetrahydrofuran
  7. customAfter 15 minutes the tetrahydrofuran was removed in vacuo
  8. extractionextracted with ethyl acetate
  9. washThe extracts were washed with water
  10. dry with materialdried over MgSO4
  11. customevaporated
  12. customto give the solid product which
  13. customwas triturated with chloroform-petroleum ether
  14. customdried under high vacuum

Sources & evidence

ORD record
ord-cf4f5462a7154e18b58080d005aa0791
Source dataset
uspto-grants-1976_06
Patent number
US03960852

Reaction notes

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