1-Butanol → Cefadroxil monohydrate

HRID 2164460Notes

Reaction equation

HRID 2164460 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 and 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-2e513b7f680043cc8c2c63107e2035a7
Source dataset
uspto-grants-1985_03
Patent number
US04504657

Reaction notes

Loading…