Pyridine → HCID 70559756, compound

HRID 461946Notes

Reaction equation

HRID 461946 reaction equation
O(CC([NH:11][CH:12]1[C:23](=[O:24])[N:14]2[CH:15]([C:20]([O-:22])=[O:21])[C:16](=[CH2:19])[CH2:17][S:18][C@H:13]12)=O)C1C=CC=CC=1.[CH2:25](Cl)[Cl:26].N1C=[CH:32][CH:31]=[CH:30][CH:29]=1.P(Cl)(Cl)(Cl)(Cl)Cl.[CH2:40]([OH:44])[CH:41](C)[CH3:42]>>[ClH:26].[NH2:11][CH:12]1[C:23](=[O:24])[N:14]2[CH:15]([C:20]([O:22][CH2:32][C:31]3[CH:42]=[CH:41][C:40]([O:44][CH3:25])=[CH:29][CH:30]=3)=[O:21])[C:16](=[CH2:19])[CH2:17][S:18][C@H:13]12

Participants

6

Reactant 5

HCID 1049PyridineHCID 6344DichloromethaneHCID 6560IsobutanolHCID 24819Phosphorus pentachlorideHCID 86735300HCID 86735300, compound

Product 1

HCID 70559756HCID 70559756, compound

Procedure

To a solution of 4.3 g. of p-methoxybenxyl 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-methoxybenzy 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. customp-methoxybenzy 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-ec3db923d05f47248bb965a7277aa3de
Source dataset
uspto-grants-1977_12
Patent number
US04064343

Reaction notes

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