Pyridine → HCID 131710674, compound

HRID 596839Notes

Reaction equation

HRID 596839 reaction equation
S1C=CC=C1CC([NH:9][CH:10]1[C:36](=[O:37])[N:12]2[C:13]([C:20]([O:22][CH:23]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])=[C:14]([C:17](=[O:19])[CH3:18])[CH2:15][S:16][C@H:11]12)=O.C(Cl)Cl.N1C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl>C(OCC)(=O)C.C(=O)(O)[O-].[Na+].CCCCCC.C(O)C(C)C>[NH2:9][CH:10]1[C:36](=[O:37])[N:12]2[C:13]([C:20]([O:22][CH:23]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])=[C:14]([C:17](=[O:19])[CH3:18])[CH2:15][S:16][C@H:11]12

Participants

9

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 24819Phosphorus pentachlorideHCID 70636138HCID 70636138, compound

Product 1

HCID 131710674HCID 131710674, compoundYield 77.9%

Reagents, catalysts & solvents 4

HCID 6560IsobutanolSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a slurry of 0.457 g. of benzhydryl 7-(2-thienylacetamido)-3-acetyl-3-cephem-4-carboxylate in 5 ml. of methylene chloride was added .085 ml. of pyridine and 0.205 g. of phosphorous pentachloride. The reaction mixture was allowed to stir for two hours at room temperature. After cooling the reaction mixture briefly in an ice bath 0.425 ml. of isobutanol was added. After allowing the reaction mixture to stir at room temperature for one hour n-hexane was added dropwise causing a precipitate which, after cooling the reaction mixture briefly in an ice bath, was isolated by decanting the supernatant liquid. The product thereby isolated was dissolved in a slurry of ethyl acetate and aqueous sodium bicarbonate. The organic layer was separated, washed with aqueous sodium bicarbonate solution and brine and then dried over anhydrous sodium sulfate. Evaporation in vacuo to dryness provided 0.270 g. (77.9 percent) of title product as a brown froth:

Workup

  1. temperatureAfter cooling the reaction mixture briefly in an ice bath 0.425 ml
  2. additionwas added dropwise
  3. temperatureafter cooling the reaction mixture briefly in an ice bath
  4. customwas isolated
  5. customby decanting the supernatant liquid
  6. customThe product thereby isolated
  7. customThe organic layer was separated
  8. washwashed with aqueous sodium bicarbonate solution and brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. customEvaporation in vacuo to dryness
  11. customprovided 0.270 g

Sources & evidence

ORD record
ord-275faf183ef84cc1a6bdb5f150789d1e
Source dataset
uspto-grants-1977_03
Patent number
US04012380

Reaction notes

Loading…