Sodium Chloride → HCID 178474495, compound

HRID 1448033Notes

Reaction equation

HRID 1448033 reaction equation
[Br:1][CH2:2][C:3](=[O:42])[CH2:4][C:5]([NH:7][CH:8]1[C:40](=[O:41])[N:10]2[C:11]([C:24]([O:26][CH:27]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])=[C:12]([C:15]3[S:16][C:17]([NH:20][C:21](=[O:23])[CH3:22])=[N:18][N:19]=3)[CH2:13][S:14][C@H:9]12)=[O:6].[N:43]([O-])=[O:44].[Na+].[Cl-].[Na+]>C(O)(=O)C.O>[Br:1][CH2:2][C:3](=[O:42])[C:4](=[N:43][OH:44])[C:5]([NH:7][CH:8]1[C:40](=[O:41])[N:10]2[C:11]([C:24]([O:26][CH:27]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[O:25])=[C:12]([C:15]3[S:16][C:17]([NH:20][C:21](=[O:23])[CH3:22])=[N:18][N:19]=3)[CH2:13][S:14][C@H:9]12)=[O:6]

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 23668193Sodium NitriteHCID 88790938HCID 88790938, compound

Product 1

HCID 178474495HCID 178474495, compoundYield 89.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

In 4 ml of acetic acid there was dissolved 0.37 g of benzhydryl 7-(4-bromo-3-oxobutyrylamino)-3-(5-acetylamino-1,3,4-thiadiazol-2-yl)-3-cephem-4-carboxylate and, under ice-cooling and stirring, a solution of 0.048 g of sodium nitrite in 0.4 ml of water was added dropwise. After this dropwise addition, the mixture was stirred at room temperature for one hour. Then, 20 ml of a saturated aqueous solution of sodium chloride were added and extraction was carried out with ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solvent was evaporated off under reduced pressure and the residue was loosened up with a solvent mixture of petroleum ether and ether (2:1 volume/volume). The resultant powder was recovered by filtration and dried. By the above procedure there was obtained 0.345 g of benzhydryl 7-(4-bromo-3-oxo-2-hydroxyiminobutyrylamino)-3-(5-acetylamino-1,3,4-thiadiazol-2-yl)-3-cephem-4-carboxylate-(syn-isomer).

Workup

  1. temperatureunder ice-cooling
  2. additionAfter this dropwise addition
  3. stirringthe mixture was stirred at room temperature for one hour
  4. extractionextraction
  5. washThe ethyl acetate layer was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated off under reduced pressure
  8. additionthe residue was loosened up with a solvent mixture of petroleum ether and ether (2:1 volume/volume)
  9. filtrationThe resultant powder was recovered by filtration
  10. customdried

Sources & evidence

ORD record
ord-a2dea41301c44ad28c1d6452aedfd414
Source dataset
uspto-grants-1979_12
Patent number
US04179502

Reaction notes

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