Pyridine → HCID 131715965, compound

HRID 1904651Notes

Reaction equation

HRID 1904651 reaction equation
C1(CC([NH:10][CH:11]2[C:38](=[O:39])[N:13]3[C:14]([C:26]([O:28]CC4C=CC(OC)=CC=4)=[O:27])=[C:15]([CH:18]=[CH:19][C:20]4[S:24][CH:23]=[N:22][C:21]=4[CH3:25])[CH2:16][S:17][C@H:12]23)=O)C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl.N1C=CC=CC=1.[Cl-].[Na+]>C(Cl)Cl.CO>[NH2:10][CH:11]1[C:38](=[O:39])[N:13]2[C:14]([C:26]([OH:28])=[O:27])=[C:15]([CH:18]=[CH:19][C:20]3[S:24][CH:23]=[N:22][C:21]=3[CH3:25])[CH2:16][S:17][C@H:12]12

Participants

7

Reactant 4

HCID 1049PyridineHCID 5234Sodium ChlorideHCID 24819Phosphorus pentachlorideHCID 131715966HCID 131715966, compound

Product 1

HCID 131715965HCID 131715965, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-30 °C

Procedure

p-Methoxybenzyl 7-phenylacetamido-3-[2-(4-methylthiazol-5-yl)vinyl]-3-cephem-4-carboxylate (trans-isomer) (0.720 g, 1.28 mmol) was dissolved in methylene chloride (3 ml). The resultant solution was poured into a solution of phosphorus pentachloride (0.800 g, 3.84 mmol) and pyridine (1.04 ml, 12.8 mmol) in methylene chloride (20 ml) at -30° C. The resultant solution was stirred for 3 hours under ice-cooling and poured into methanol (20 ml) as pre-cooled to -30° C., followed by stirring the mixture for 1 hour at ambient temperature. The reaction solution obtained was poured into a mixture of aqueous saturated sodium chloride solution (20 ml) and methylene chloride (20 ml), and the resulting mixture was stirred for 1 hour. The mixture was cooled to stand until it separated into the aqueous phase and organic solvent phase. The aqueous phase separated out was extracted with methylene chloride (20 ml) and the methylene chloride extract was combined with the organic phase mentioned above. The combined organic phase was washed with aqueous saturated sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue obtained was purified chromatographically on a column of silica gel (Wako gel C-300) (20 g) as developed with benzene-ethyl acetate (3:1) as the development solvent. The titled compound, 7-amino-3-[2-(4-methylthiazol-5-yl)vinyl]-3-cephem-4-carboxylic acid (trans-isomer) p-methoxybenzyl ester (0.443 g, 78%) was obtained.

Workup

  1. temperaturecooling
  2. customThe reaction solution obtained
  3. stirringthe resulting mixture was stirred for 1 hour
  4. temperatureThe mixture was cooled
  5. customseparated into the aqueous phase and organic solvent phase
  6. customThe aqueous phase separated out
  7. extractionwas extracted with methylene chloride (20 ml)
  8. extractionthe methylene chloride extract
  9. washThe combined organic phase was washed with aqueous saturated sodium hydrogen carbonate solution
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customThe residue obtained
  13. customwas purified chromatographically on a column of silica gel (Wako gel C-300) (20 g)

Sources & evidence

ORD record
ord-33bf5b9159fb43ad896fbb13d992da03
Source dataset
uspto-grants-1989_06
Patent number
US04839350

Reaction notes

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