Hydrochloric Acid → Cephradine

HRID 1197759Notes

Reaction equation

HRID 1197759 reaction equation
[CH3:1][C:2]1[CH2:21][S:20][C@@H:5]2[C@H:6]([NH:9][C:10]([C@H:12]([NH2:19])[C:13]3[CH2:18][CH:17]=[CH:16][CH2:15][CH:14]=3)=[O:11])[C:7](=[O:8])[N:4]2[C:3]=1[C:22]([OH:24])=[O:23].CN(C)C=O.Cl>O>[CH3:1][C:2]1[CH2:21][S:20][C@@H:5]2[C@H:6]([NH:9][C:10]([C@H:12]([NH2:19])[C:13]3[CH2:18][CH:17]=[CH:16][CH2:15][CH:14]=3)=[O:11])[C:7](=[O:8])[N:4]2[C:3]=1[C:22]([OH:24])=[O:23]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 86747480Cephradine Dimethylformamide

Product 1

HCID 38103Cephradine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

125 g of cephradine dimethylformamide solvate (as for example produced in step a) above) were suspended in water/conc. HCl (300/12.5) at 5° to 10° C. with stirring. The pH was adjusted to 1.6 to 2.0 by addition of hydrochloric acid in order to obtain a complete solution. The solution was filtered and the residue washed with 60 ml of water. The combined filtrate was warmed to 35° to 40° C. The pH was adjusted to 2.4 to 2.8 with triethylamine whereupon precipitation started. The stirring was maintained for several minutes. The pH was then adjusted to 4.7 to 5.1 with triethylamine and the suspension was cooled to about 25° and filtered. The residue was washed with 270 g of acetone (80% v/v) to obtain the heading compound, m.p. 190° to 200° C. (decomp.).

Workup

  1. customto obtain a complete solution
  2. filtrationThe solution was filtered
  3. washthe residue washed with 60 ml of water
  4. temperatureThe combined filtrate was warmed to 35° to 40° C
  5. customThe pH was adjusted to 2.4 to 2.8 with triethylamine whereupon precipitation
  6. temperatureThe stirring was maintained for several minutes
  7. temperaturethe suspension was cooled to about 25°
  8. filtrationfiltered
  9. washThe residue was washed with 270 g of acetone (80% v/v)
  10. customto obtain the heading compound, m.p. 190° to 200° C. (decomp.)

Sources & evidence

ORD record
ord-f41ee769477f4d07980b8ca654185518
Source dataset
uspto-grants-1994_01
Patent number
US05278157

Reaction notes

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