p-Toluenesulfonic acid → HCID 131710313, compound

HRID 1657733Notes

Reaction equation

HRID 1657733 reaction equation
O(CC([NH:11][CH:12]1[C:32](=[O:33])[N:14]2[CH:15]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)=[O:21])[C:16](=[CH2:19])[CH2:17][S:18][C@H:13]12)=O)C1C=CC=CC=1.C(Cl)Cl.P(Cl)(Cl)(Cl)(Cl)Cl.[C:43]1([CH3:53])[CH:48]=[CH:47][C:46]([S:49]([OH:52])(=[O:51])=[O:50])=[CH:45][CH:44]=1>C(OCC)(=O)C.CO.N1C=CC=CC=1>[C:43]1([CH3:53])[CH:44]=[CH:45][C:46]([S:49]([OH:52])(=[O:50])=[O:51])=[CH:47][CH:48]=1.[NH2:11][CH:12]1[C:32](=[O:33])[N:14]2[CH:15]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)=[O:21])[C:16](=[CH2:19])[CH2:17][S:18][C@H:13]12

Participants

8

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 6344DichloromethaneHCID 24819Phosphorus pentachlorideHCID 12877287HCID 12877287, compound

Product 1

HCID 131710313HCID 131710313, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 937 mg. of p-methoxybenzyl 7-phenoxyacetamido-3-methylenecepham-4-carboxylate in 10 ml. of methylene chloride was added 0.18 ml. of dry pyridine and 460 mg. of phosphorus pentachloride. The mixture was stirred at room temperature for 2 hours and was then cooled to 5°C. To the cold mixture was added 50 ml. of cold methanol and the mixture was allowed to warm to room temperature. The reaction mixture was evaporated in vacuo and the residue was dissolved in a mixture of ethyl acetate and water. The pH of the solution was adjusted to pH 7 and the ethyl acetate layer was separated, washed with water and dried. To the dried ethyl acetate layer was added one equivalent of p-toluene sulfonic acid. On cooling 600 mg. of p-methoxybenzyl 3-methylenecepham-4-carboxylate p-toluenesulfonate precipitated as a crystalline solid.

Workup

  1. temperaturewas then cooled to 5°C
  2. additionTo the cold mixture was added 50 ml
  3. temperatureto warm to room temperature
  4. customThe reaction mixture was evaporated in vacuo
  5. dissolutionthe residue was dissolved in a mixture of ethyl acetate and water
  6. customthe ethyl acetate layer was separated
  7. washwashed with water
  8. customdried
  9. temperatureOn cooling 600 mg
  10. customof p-methoxybenzyl 3-methylenecepham-4-carboxylate p-toluenesulfonate precipitated as a crystalline solid

Sources & evidence

ORD record
ord-fc463ca5be8f4c5bae49136a1322c330
Source dataset
uspto-grants-1976_06
Patent number
US03962227

Reaction notes

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