Methane → Cefadroxil monohydrate

HRID 224936Notes

Reaction equation

HRID 224936 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.Cl.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

5

Reactant 3

HCID 297MethaneHCID 313Hydrochloric AcidHCID 86754917HCID 86754917, compound

Product 1

HCID 47964Cefadroxil monohydrateYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Cefadroxil DMF solvate (50 g.; ~0.105 mole) was dissolved in 150 ml. water and 8.8 ml. HCl (36%). Charcoal (2.7 g.) and Celite (1.35 g.) were then added. After 30 minutes of stirring, the mixture was filtered through a Celite pad and washed with water. The filtered solution was heated to 40° and the pH adjusted to 2.5 with triethylamine. The mixture was then seeded with crystals of cefadroxil monohydrate and the pH adjusted to 4.5 with triethylamine. The suspension was stirred for one hour at 50° and progressively cooled to room temperature and then maintained for one hour at 0° to +5°. The crystalline cefadroxil monohydrate was collected, washed twice with cold water and dried at 40° to yield 30.8 g. (~76-77% yield) of product having the same physical characteristics as described in Example 1.

Workup

  1. filtrationthe mixture was filtered through a Celite pad
  2. washwashed with water
  3. temperatureThe filtered solution was heated to 40°
  4. stirringThe suspension was stirred for one hour at 50°
  5. temperaturemaintained for one hour at 0° to +5°
  6. customThe crystalline cefadroxil monohydrate was collected
  7. washwashed twice with cold water
  8. customdried at 40°
  9. customto yield 30.8 g

Sources & evidence

ORD record
ord-2a3a8b3773ab486ba601ca5b0a14aa89
Source dataset
uspto-grants-1980_11
Patent number
US04234721

Reaction notes

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