1-Butanol → Cefadroxil monohydrate

HRID 224937Notes

Reaction equation

HRID 224937 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-1feb25e769314f62b9a7798fc88d5d74
Source dataset
uspto-grants-1980_11
Patent number
US04234721

Reaction notes

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