HCID 86754917, compound → Cefadroxil monohydrate

HRID 2198556Notes

Reaction equation

HRID 2198556 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].CN(C=[O:30])C>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

3

Reactant 1

HCID 86754917HCID 86754917, compound

Product 1

HCID 47964Cefadroxil monohydrate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The DMF-solvate of Step C was added in portions and with stirring in about 10 minutes to 175 ml of distilled water at room temperature. After the addition and dissolution of 5 g of the solvate, 1 g of seeding crystals of cefadroxil-monohydrate were added to the mixture. After the complete addition, stirring was continued for one hour and the pyramidal crystals were filtered and washed with water at 0° C. and dried under vacuo at about 30° C. to obtain 35.4 g of crystalline white cefadroxil monohydrate. The structure of the compound was confirmed by IR and PMR spectra and showed a high purity of the product. The mother liquor was evaporated to 50 ml and after addition of 600 ml of DMF, 21.3 g of the same solvate were recovered for an overall yield of 78% of cefadroxil based on the starting 7-ADCA.

Workup

  1. additionAfter the addition and dissolution of 5 g of the solvate, 1 g
  2. additionwere added to the mixture
  3. additionAfter the complete addition
  4. filtrationthe pyramidal crystals were filtered
  5. washwashed with water at 0° C.
  6. customdried under vacuo at about 30° C.

Sources & evidence

ORD record
ord-db1d44b193904eefa6749b32c3c623c5
Source dataset
uspto-grants-1982_11
Patent number
US04358588

Reaction notes

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