Hydrochloric Acid → benzhydryl 7-phenoxyacetamido-3-(1-methyl-1H-tetrazol-5-yl)vinyl-3-cephem-4-carboxylate-1-oxide

HRID 26041Notes

Reaction equation

HRID 26041 reaction equation
O1CCCC1.[O:6]([CH2:13][C:14]([NH:16][CH:17]1[C:43](=[O:44])[N:19]2[C:20]([C:27]([O:29][CH:30]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[O:28])=[C:21]([CH:25]=O)[CH2:22][S:23](=[O:24])[C@H:18]12)=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:45][N:46]1[C:50]([CH:51]=P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[N:49][N:48]=[N:47]1.Cl>CO.C(OCC)(=O)C>[O:6]([CH2:13][C:14]([NH:16][CH:17]1[C:43](=[O:44])[N:19]2[C:20]([C:27]([O:29][CH:30]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[O:28])=[C:21]([CH:25]=[CH:51][C:50]3[N:46]([CH3:45])[N:47]=[N:48][N:49]=3)[CH2:22][S:23](=[O:24])[C@H:18]12)=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 213262271-Methyl-5-[(triphenyl-lambda~5~-phosphanylidene)methyl]-1H-tetrazoleHCID 88791210Benzhydryl 7-phenoxyacetamido-3-formyl-3-cephem-4-carboxylate-1-oxide

Product 1

HCID 131711473benzhydryl 7-phenoxyacetamido-3-(1-methyl-1H-tetrazol-5-yl)vinyl-3-cephem-4-carboxylate-1-oxideYield 59%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 130 ml of anhydrous tetrahydrofuran was added 5.35 g of benzhydryl 7-phenoxyacetamido-3-formyl-3-cephem-4-carboxylate-1-oxide, and, after cooling to -5°--10° C., further added 4.3 g of (1-methyl-1H-tetrazol-5-yl)methylenetriphenylphosphorane. The mixture was stirred at that temperature for 5 hours and poured into a mixture of ethyl acetate and ice-water. The resulting mixture was then made acidic with 10 ml of 5% hydrochloric acid. The organic layer was washed with five portions of a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to leave a solid residue. The residue was, after addition of approximately 30 ml of methanol, stirred at room temperature for 20 minutes and filtered leaving a precipitate. There was obtained 3.62 g of benzhydryl 7-phenoxyacetamido-3-(1-methyl-1H-tetrazol-5-yl)vinyl-3-cephem-4-carboxylate-1-oxide as a crystalline powder. The filtrate was evaporated under redueced pressure to dryness, and the obtained residue was developed through silica gel column with ethyl acetate to give 600 mg of the crystals additionally.

Workup

  1. temperatureafter cooling to -5°--10° C.
  2. washThe organic layer was washed with five portions of a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customto leave a solid residue
  6. stirringstirred at room temperature for 20 minutes
  7. filtrationfiltered
  8. customleaving a precipitate

Sources & evidence

ORD record
ord-9c598c52791e4c86b00112de07b5a010
Source dataset
uspto-grants-1979_04
Patent number
US04147863

Reaction notes

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