Pyridine → Hydrochloric Acid

HRID 1729543Notes

Reaction equation

HRID 1729543 reaction equation
C1(CC([NH:10][CH:11]2[C:39](=[O:40])[N:13]3[C:14]([C:23]([O:25][CH:26]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[S:24])=[C:15]([CH:18]4[CH2:22][CH2:21][O:20][CH2:19]4)[CH2:16][S:17][C@H:12]23)=O)C=CC=CC=1.N1C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)[Cl:48].C(OC(C)C)(C)C>ClCCl.O.CO>[NH2:10][CH:11]1[C:39](=[O:40])[N:13]2[C:14]([C:23]([O:25][CH:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[S:24])=[C:15]([CH:18]3[CH2:22][CH2:21][O:20][CH2:19]3)[CH2:16][S:17][C@H:12]12.[ClH:48]

Participants

9

Reactant 4

HCID 1049PyridineHCID 7914Diisopropyl EtherHCID 24819Phosphorus pentachlorideHCID 131718571HCID 131718571, compound

Product 2

HCID 313Hydrochloric AcidYield 53%HCID 131718570HCID 131718570, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-20 °C

Procedure

Diphenylmethyl 7-phenylacetamido-3-(tetrahydrofuran-3-yl)thio-3-cephem-4-carboxylate (590 mg) was suspended in dichloromethane (8 ml) and the suspension was cooled to -20° C. To the cooled suspension were added pyridine (0.24 ml) and phosphorus pentachloride, and the resulting mixture was stirred under ice-cooling for 2 hours and then cooled again to -20° C. Anhydrous methanol (0.81 ml) was then added rapidly and the mixture was stirred under ice-cooling for 3 hours. Cold water (10 ml) and dichloromethane(5 ml) were added to the resulting reaction solution, and the solution was stirred under ice-cooling for 30 minutes to deposit crystals. The mixture containing the crystals, after adding diisopropylether (10 ml) thereto, was stirred well and then filtered to obtain the crystals. The crystals were washed with cold water and with a small amount of dichloromethane, successively and then dried to afford the titled compound in the form of hydrochloride (270 mg; 53%) as pale yellow power.

Workup

  1. temperaturecooling for 2 hours
  2. temperaturecooled again to -20° C
  3. stirringthe mixture was stirred under ice-
  4. temperaturecooling for 3 hours
  5. stirringthe solution was stirred under ice-
  6. temperaturecooling for 30 minutes
  7. additionThe mixture containing the crystals
  8. stirringwas stirred well
  9. filtrationfiltered
  10. customto obtain the crystals
  11. washThe crystals were washed with cold water and with a small amount of dichloromethane
  12. customsuccessively and then dried

Sources & evidence

ORD record
ord-e861b662dadb420ab8d443443f18e611
Source dataset
uspto-grants-1994_07
Patent number
US05332731

Reaction notes

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