Pyridine → HCID 14672337, compound

HRID 2108209Notes

Reaction equation

HRID 2108209 reaction equation
C1(CC([NH:10][C@@H:11]2[C:37](=[O:38])[N:13]3[C:14]([C:25]([O:27][CH2:28][C:29]4[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=4)=[O:26])=[C:15]([S:18]/[CH:19]=[CH:20]\[C:21]([O:23][CH3:24])=[O:22])[CH2:16][S:17][C@H:12]23)=O)C=CC=CC=1.N1C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>ClCCl.O.CO>[NH2:10][C@@H:11]1[C:37](=[O:38])[N:13]2[C:14]([C:25]([O:27][CH2:28][C:29]3[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=3)=[O:26])=[C:15]([S:18]/[CH:19]=[CH:20]\[C:21]([O:23][CH3:24])=[O:22])[CH2:16][S:17][C@H:12]12

Participants

8

Reactant 4

HCID 1049PyridineHCID 24819Phosphorus pentachlorideHCID 516892Sodium BicarbonateHCID 14672335HCID 14672335, compound

Product 1

HCID 14672337HCID 14672337, compoundYield 73.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of 18.3 g (33.0 mM) of 4-methoxybenzyl 7β-phenylacetamido-3-[(Z)-2-methoxycarbonylvinylthio]-3-cephem-4-carboxylate in 200 ml of dry dichloromethane were added 7.82 g (99.0 mM) of pyridine and 13.7 g (65.8 mM) of phosphorus pentachloride, and the reaction temperature was raised to room temperature for a period of 30 minutes, and the mixture was stirred at the same temperature for 1 hour. To the cooled (-50° C.) reaction solution was added 100 ml of dry methanol, and the mixture was stirred at -20° C. for 1 hour. Upon continued cooling of the reaction mixture to -50° C., 100 ml of water was added, and the mixture was stirred under ice-cooling for 40 minutes. The mixture was made weakly basic by addition of a saturated aqueous sodium bicarbonate solution, and extracted with 300 ml of ethyl acetate, and the extract was washed with 200 ml of a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was evaporated, and diethyl ether was added to the residue for powdering to give 10.6 g of 4-methoxybenzyl 7β-amino-3-[(Z)-2-methoxycarbonylvinylthio]-3-cephem-4-carboxylate.

Workup

  1. temperatureTo the cooled
  2. custom(-50° C.) reaction solution
  3. stirringthe mixture was stirred at -20° C. for 1 hour
  4. temperatureUpon continued cooling of the reaction mixture to -50° C.
  5. stirringthe mixture was stirred under ice-
  6. temperaturecooling for 40 minutes
  7. extractionextracted with 300 ml of ethyl acetate
  8. washthe extract was washed with 200 ml of a saturated aqueous sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThe solvent was evaporated
  11. additiondiethyl ether was added to the residue

Sources & evidence

ORD record
ord-541530daf928406a9ca39bffc96f6113
Source dataset
uspto-grants-1990_06
Patent number
US04937332

Reaction notes

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