N-methyl-2-pyrrolidone → Cefadroxil hemihydrate

HRID 1200207Notes

Reaction equation

HRID 1200207 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].CC(N(C)C)=[O:28].CN1CCCC1=O.CNC=O>O.CO.C(O)(C)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].[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].[OH2:28]

Participants

7

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 31254N-MethylformamideHCID 31374DimethylacetamideHCID 47965Cefadroxil

Product 1

HCID 67173987Cefadroxil hemihydrate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21255859Isopropanol methanolSolvent

Procedure

Consequently the present invention relates to a method for producing crystalline cefadroxil hemihydrate, according to which a cefadroxil solvate of dimethylacetamide, of N-methyl-2-pyrrolidone or of monomethylformamide is slurried with a mixture methanol:isopropyl alcohol 30:7: to 70:30 by volume containing from 5% to 12% of water, at a temperature in the range of about +45° C. to +55° C. and then isolating the so obtained crystalline cefadroxil hemihydrate.

Sources & evidence

ORD record
ord-594a95aea4b2430c951b99811ced5131
Source dataset
uspto-grants-1990_02
Patent number
US04904776

Reaction notes

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