Hydrochloric Acid → Loracarbef

HRID 35994Notes

Reaction equation

HRID 35994 reaction equation
[CH2:1]1[CH:6]2[CH:7]([NH:10][C:11]([C@H:13]([NH2:20])[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:12])[C:8](=[O:9])[N:5]2[C:4]([C:21]([OH:23])=[O:22])=[C:3]([Cl:24])[CH2:2]1.O.Cl.OC1C=CC(C(OCC)=O)=CC=1>C(O)C>[CH:17]1[CH:16]=[CH:15][C:14]([C@@H:13]([NH2:20])[C:11]([NH:10][C@@H:7]2[C:8](=[O:9])[N:5]3[C@@H:6]2[CH2:1][CH2:2][C:3]([Cl:24])=[C:4]3[C:21]([OH:23])=[O:22])=[O:12])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8434EthylparabenHCID 60746Loribid2×

Product 1

HCID 5284585LoracarbefYield 98.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The pH of aqueous loracarbef monohydrate mother liquor (1000 ml, having 9.23 mg/ml of loracarbef monohydrate) was adjusted to 3.6 with HCl. Ethyl p-hydroxybenzoate (ethyl paraben) (4.52g) in ethanol (36 ml) was added dropwise over 15 minutes. After approximately 5 minutes, precipitation occurred, resulting in white crystals. The mixture was stirred overnight (15 hrs) at room temperature, filtered, washed with H2O, and dried under vacuum at 40° C. The yield was 11.72 g having a potency of 73.5% as loracarbef, and the theoretical yield was 8.78 g as loracarbef, resulting in a percent yield of 98.2%. The loracarbef:ethyl paraben exhibited the following X-ray powder diffraction pattern:

Workup

  1. customprecipitation
  2. customresulting in white crystals
  3. filtrationfiltered
  4. washwashed with H2O
  5. customdried under vacuum at 40° C

Sources & evidence

ORD record
ord-c1391ba1d49f4dff8810856adbb36b69
Source dataset
uspto-grants-1995_05
Patent number
US05412094

Reaction notes

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