1-Butanol → Cefadroxil monohydrate

HRID 971721Notes

Reaction equation

HRID 971721 reaction equation
[CH3:1][C:2]1[CH2:22][S:21][C@@H:5]2[C@H:6]([NH:9][C:10]([C@H:12]([NH2:20])[C:13]3[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=3)=[O:11])[C:7](=[O:8])[N:4]2[C:3]=1[C:23]([OH:25])=[O:24].C([OH:30])CCC>O>[CH3:1][C:2]1[CH2:22][S:21][C@@H:5]2[C@H:6]([NH:9][C:10]([C@H:12]([NH2:20])[C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)=[O:11])[C:7](=[O:8])[N:4]2[C:3]=1[C:23]([OH:25])=[O:24].[OH2:30]

Participants

4

Reactant 2

HCID 2631-ButanolHCID 47965Cefadroxil2×

Product 1

HCID 47964Cefadroxil monohydrateYield 82.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Primary grade cefadroxil (11.7 g.) was added to a 48° C. mixture of 8.35 ml. water and 7.0 ml. n-butanol in 1 g. increments over a two hour period. The reaction mixture was initially seeded with crystals of cefadroxil.H2O was stirred during the two hour addition step. The crystal slurry was allowed to cool to room temperature (approximately two hours) and was filtered. The filter cake was washed with n-butanol, water and isopropanol and dried to give 9.4 g. (82.7%) of title product. Biopotency=940 mcg./mg. K.F.=5.3%. Chemical potency=966 mcg./mg.

Workup

  1. additionmixture of 8.35 ml
  2. filtrationwas filtered
  3. washThe filter cake was washed with n-butanol, water and isopropanol
  4. customdried
  5. customto give 9.4 g

Sources & evidence

ORD record
ord-c5b68e8572c74d25bafd60c2cae851cd
Source dataset
uspto-grants-1979_07
Patent number
US04160863

Reaction notes

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