Water → Cefadroxil monohydrate

HRID 971720Notes

Reaction equation

HRID 971720 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].[OH2:26]>C(#N)C>[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].[OH2:26]

Participants

4

Reactant 2

HCID 962Water2×HCID 47965Cefadroxil2×

Product 1

HCID 47964Cefadroxil monohydrateYield 81.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Primary grade cefadroxil (8.0 g.) was added in 1 gram increments to a mixture of 5 ml. water and 5 ml. acetonitrile at 40° C. over a 45 minute period. The solution was seeded initially by addition of cefadroxil.H2O crystals. The reaction mixture was stirred for 15 minutes followed by addition of 10 ml. of acetonitrile over 15 minutes. The crystal slurry was allowed to cool to room temperature (approximately 3 hours) and was then filtered. The filter cake was washed with 7 ml. of acetonitrile:water (3:1) and dried to give 6.25 g. (81.5%) of title product. Biopotency=950 mcg./mg. K.F.=4.7%. Chemical potency=965 mcg./mg.

Workup

  1. additionfollowed by addition of 10 ml
  2. filtrationwas then filtered
  3. washThe filter cake was washed with 7 ml
  4. dry with materialof acetonitrile:water (3:1) and dried
  5. customto give 6.25 g

Sources & evidence

ORD record
ord-0e675b2be7074c21a6d53788169a913a
Source dataset
uspto-grants-1979_07
Patent number
US04160863

Reaction notes

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