Pyridine → HCID 131715887, compound

HRID 1194163Notes

Reaction equation

HRID 1194163 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)=[S:26])=[C:15]([CH2:18][CH2:19][O:20][C:21](=[O:24])[CH2:22][Cl:23])[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)=[S:26])=[C:15]([CH2:18][CH2:19][O:20][C:21](=[O:24])[CH2:22][Cl:23])[CH2:16][S:17][C@H:12]12

Participants

8

Reactant 4

HCID 1049PyridineHCID 24819Phosphorus pentachlorideHCID 516892Sodium BicarbonateHCID 131715888HCID 131715888, compound

Product 1

HCID 131715887HCID 131715887, compoundYield 90.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-50 °C

Procedure

In 50 ml of dry dichloromethane was dissolved 1.70 g (2.88 mM) of p-methoxybenzyl 7β-phenylacetamido-3-(2-chloroacetyloxy)ethylthio-3-cephem-4-carboxylate, and the solution was cooled to -50° C. To the solution were added 0.706 ml (8.64 mM) of pyridine and 1.196 g (5.76 mM) of phosphorus pentachloride, the reaction temperature of the mixture was raised to 20° C. for a period of one hour, and the mixture was stirred at the same temperature for one hour. Then, the reaction mixture was cooled to -50° C., 10 ml of dry methanol was added, and the temperature of the mixture was raised to 0° C. for a period of one hour. To the reaction mixture cooled to -5° C. was added 10 ml of water, and the mixture was stirred under ice-cooling for 40 minutes. The mixture was made neutral by addition of a saturated aqueous sodium bicarbonate solution, the organic layer was washed with a saturated aqueous sodium chloride solution (10 ml×3) and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (eluent, dichloromethane) to give 1.22 g of p-methoxybenzyl 7β-amino-3-(2-chloroacetyloxy)ethylthio-3-cephem-4-carboxylate.

Workup

  1. temperaturethe reaction temperature of the mixture was raised to 20° C. for a period of one hour
  2. temperatureThen, the reaction mixture was cooled to -50° C.
  3. temperaturethe temperature of the mixture was raised to 0° C. for a period of one hour
  4. temperatureTo the reaction mixture cooled to -5° C.
  5. stirringthe mixture was stirred under ice-
  6. temperaturecooling for 40 minutes
  7. washthe organic layer was washed with a saturated aqueous sodium chloride solution (10 ml×3)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was evaporated
  10. customthe residue was purified by silica gel column chromatography (eluent, dichloromethane)

Sources & evidence

ORD record
ord-7348cb3dd27e4e9d9b086635e3321407
Source dataset
uspto-grants-1989_03
Patent number
US04812562

Reaction notes

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