Quinoline → HCID 131711475, compound

HRID 26043Notes

Reaction equation

HRID 26043 reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].N1C2C(=CC=CC=2)C=CC=1.O(CC([NH:27][CH:28]1[C:59](=[O:60])[N:30]2[C:31]([C:43]([O:45][CH:46]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)[C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)=[O:44])=[C:32]([CH:35]=[CH:36][C:37]3[N:41]([CH3:42])[N:40]=[N:39][N:38]=3)[CH2:33][S:34][C@H:29]12)=O)C1C=CC=CC=1>C(Cl)(Cl)Cl.C(O)CC>[ClH:2].[NH2:27][CH:28]1[C:59](=[O:60])[N:30]2[C:31]([C:43]([O:45][CH:46]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)[C:47]3[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=3)=[O:44])=[C:32]([CH:35]=[CH:36][C:37]3[N:41]([CH3:42])[N:40]=[N:39][N:38]=3)[CH2:33][S:34][C@H:29]12

Participants

6

Reactant 3

HCID 7047QuinolineHCID 24819Phosphorus pentachloride2×HCID 131711474HCID 131711474, compound

Product 1

HCID 131711475HCID 131711475, compoundYield 57.4%

Reagents, catalysts & solvents 2

HCID 10311-PropanolSolventHCID 6212ChloroformSolvent2×

Procedure

To 15 ml of chloroform was added 1.218 g of phosphorus pentachloride, and the phosphorus pentachloride was dissolved therein by warming. To the solution maintained at 10°-20° C. was added 0.929 g of quinoline. Five minutes later, the temperature was lowered to -10°--20° C., and to the mixture was added 2.7 g of benzhydryl 7-phenoxyacetamido-3-(1-methyl-1H-tetrazol-5-yl)vinyl-3-cephem-4-carboxylate. The mixture was then stirred for 10 minutes and at room temperature for one hour. The mixture was then cooled to 0° C., and to this was added 5.4 ml of n-propanol. The resulting mixture was stirred at room temperature for one hour and poured into ice-water. To this was further added an appropriate amount of chloroform. The precipitated crystals were collected by filtration and dried to yield 1.3 g of benzhydryl 7-amino-3-(1-methyl-1H-tetrazol-5-yl)vinyl-3-cephem-4-carboxylate hydrochloride. To the obtained hydrochloride was added a mixture of a dilute aqueous sodium hydrogencarbonate solution and ethyl acetate, and the ethyl acetate layer was separated. From the ethyl acetate layer, there was obtained the 7-amino base.

Workup

  1. temperatureby warming
  2. temperatureTo the solution maintained at 10°-20° C.
  3. customFive minutes
  4. customwas lowered to -10°--20° C.
  5. temperatureThe mixture was then cooled to 0° C.
  6. stirringThe resulting mixture was stirred at room temperature for one hour
  7. filtrationThe precipitated crystals were collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-54586a485b3e452fb8200632488004cc
Source dataset
uspto-grants-1979_04
Patent number
US04147863

Reaction notes

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