Methanol → Cefadroxil

HRID 1728909Notes

Reaction equation

HRID 1728909 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].CNC=O.CO.C(O)(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]

Participants

5

Reactant 3

HCID 887MethanolHCID 3776IsopropanolHCID 14996561HCID 14996561, compound

Product 1

HCID 47965Cefadroxil

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

Cefadroxil monomethylformamide solvate (30 g) prepared according to Example 3 was slurried in 150 ml of a mixture 1:1 of methanol and isopropyl alcohol with 1% of water at 52° C. After 70' at 52° C. the mixture was cooled to 10° C., filtered and washed with acetone to yield 23.5 g of substantially anhydrous crystalline cefadroxil.

Workup

  1. filtrationfiltered
  2. washwashed with acetone

Sources & evidence

ORD record
ord-b2c5d55da4c34785bbea002c921a8555
Source dataset
uspto-grants-1994_07
Patent number
US05329001

Reaction notes

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