Sodium Chloride → Hydrochloric Acid

HRID 1729549Notes

Reaction equation

HRID 1729549 reaction equation
C1(CC([NH:10][CH:11]2[C:40](=[O:41])[N:13]3[C:14]([C:24]([O:26][CH:27]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[S:25])=[C:15]([CH:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)[CH2:16][S:17][C@H:12]23)=O)C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)[Cl:43].[Cl-].[Na+].C(=O)([O-])O.[Na+].C(OC(C)C)(C)C>ClCCl.CO.N1C=CC=CC=1>[NH2:10][CH:11]1[C:40](=[O:41])[N:13]2[C:14]([C:24]([O:26][CH:27]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[S:25])=[C:15]([CH:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)[CH2:16][S:17][C@H:12]12.[ClH:43]

Participants

10

Reactant 5

HCID 5234Sodium ChlorideHCID 7914Diisopropyl EtherHCID 24819Phosphorus pentachlorideHCID 516892Sodium BicarbonateHCID 131718587HCID 131718587, compound

Product 2

HCID 313Hydrochloric AcidYield 1,215.4%HCID 131718586HCID 131718586, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

Diphenylmethyl 7-phenylacetamido-3-(tetrahydropyran-4-yl)thio-3-cephem-4-carboxylate (1.28 g) was dissolved in dichloromethane (15 ml) and the solution was cooled to -20° C. To the solution, pyridine (0.52 ml) and phosphorus pentachloride (665 mg) were added and the resulting mixture was stirred under ice-cooling for 2 hours and then further cooled to -30° C. Anhydrous methanol (1.72 ml) was rapidly added to the cooled reaction solution while maintaining the temperature below 0° C. and the mixture was stirred under ice-cooling for 3 hours and then further cooled again to -20° C. After adding a 15% aqueous sodium chloride solution to the reaction solution, the pH thereof was adjusted to 1 with the addition of aqueous sodium hydrogen carbonate and the reaction solution was further stirred for 30 minutes. Upon subsequent addition of diisopropylether (30 ml), precipitate was deposited from the solution, taken up by filtration, washed with cold water and with diisopropylether successively and then dried to yield the titled compound in the form of hydrochloride (970 mg; 87%).

Workup

  1. temperaturecooling for 2 hours
  2. temperaturefurther cooled to -30° C
  3. temperaturewhile maintaining the temperature below 0° C.
  4. stirringthe mixture was stirred under ice-
  5. temperaturecooling for 3 hours
  6. temperaturefurther cooled again to -20° C
  7. stirringthe reaction solution was further stirred for 30 minutes
  8. filtrationtaken up by filtration
  9. washwashed with cold water and with diisopropylether successively
  10. customdried

Sources & evidence

ORD record
ord-dccf673dc2884bf6b5e21ef9c328bd8c
Source dataset
uspto-grants-1994_07
Patent number
US05332731

Reaction notes

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