Pyridine → HCID 70559756, compound

HRID 1706817Notes

Reaction equation

HRID 1706817 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:35].N1C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl>C(O)C(C)C>[ClH:35].[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

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 24819Phosphorus pentachlorideHCID 12877287HCID 12877287, compound

Product 1

HCID 70559756HCID 70559756, compound

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

Procedure

To a solution of 4.3 g. of p-methoxybenzyl 7-phenoxyacetamido-3-methylenecepham-4-carboxylate in 50 ml. of methylene chloride were added 880 mg. of dry pyridine and 2.3 g. of phosphorus pentachloride and the mixture was stirred at the reflux temperature for 3 hours. The reaction mixture was then cooled in an ice-water bath and 5 ml. of isobutanol were added. The mixture was stirred in the cold for several hours during which time 2.2 g. of the reaction product, p-methoxybenzyl 7-amino-3-methylenecepham-4-carboxylate hydrochloride, precipitated from the mixture. The product was filtered and washed with cold methylene chloride and was dried in vacuo.

Workup

  1. temperatureThe reaction mixture was then cooled in an ice-water bath
  2. customof the reaction product, p-methoxybenzyl 7-amino-3-methylenecepham-4-carboxylate hydrochloride, precipitated from the mixture
  3. filtrationThe product was filtered
  4. washwashed with cold methylene chloride
  5. customwas dried in vacuo

Sources & evidence

ORD record
ord-4f988f83a61a4d288565cd38f7759bdd
Source dataset
uspto-grants-1980_06
Patent number
US04208515

Reaction notes

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