Cefadroxil → Cefadroxil monohydrate

HRID 224935Notes

Reaction equation

HRID 224935 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)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: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].[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].[OH2:8]

Participants

4

Reactant 1

HCID 47965Cefadroxil

Product 2

HCID 47964Cefadroxil monohydrateHCID 47965Cefadroxil

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

By employing the preferred reaction conditions described above, the present invention makes possible the production of primary grade cefadroxil in yields of up to about 90% (activity yields) and subsequent conversion of said cefadroxil or its dimethylformamide solvate to cefadroxil monohydrate in activity yields of up to about 83%. Overall yields of cefadroxil monohydrate from 7-ADCA range up to about 75% without taking into account the additional ~5% yield possible if a second crop of monohydrate is recovered from the crystallization mother liquor as described below in Example 5.

Workup

  1. customthe preferred reaction conditions
  2. customin yields of

Sources & evidence

ORD record
ord-3d7ec244646149d0b606191ccece85e5
Source dataset
uspto-grants-1980_11
Patent number
US04234721

Reaction notes

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