1-Butanol → Cefadroxil monohydrate

HRID 1979641Notes

Reaction equation

HRID 1979641 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-05532dd8aa1a43fa97a5c468c65f2583
Source dataset
uspto-grants-1984_11
Patent number
USRE031730

Reaction notes

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