Perchloric Acid → Florfenicol butyrate

HRID 507490Notes

Reaction equation

HRID 507490 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C@@H:11]([OH:21])[C@H:12]([NH:15][C:16]([CH:18]([Cl:20])[Cl:19])=[O:17])[CH2:13][F:14])=[CH:9][CH:10]=1)(=[O:4])=[O:3].Cl(O)(=O)(=O)=[O:23]>C(OC(=O)CCC)(=O)CCC>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C@@H:11]([OH:21])[C@H:12]([NH:15][C:16]([CH:18]([Cl:20])[Cl:19])=[O:17])[CH2:13][F:14])=[CH:9][CH:10]=1)(=[O:4])=[O:3].[C:11]([O-:21])(=[O:23])[CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 24247Perchloric AcidHCID 114811Florfenicol

Product 1

HCID 131727111Florfenicol butyrate

Reagents, catalysts & solvents 1

HCID 7798Butyric anhydrideSolvent

Procedure

225 g of florfenicol was suspended in 330 ml of butyric anhydride in one liter round bottom flask equipped with a over head stirrer and a drying tube. To this suspension was added one ml of perchloric acid, while stirring vigorously, with a pipette. A clear solution was obtained in a few minutes. Stirring was continued for another 3 hours during which the florfenicol butyrate pro-drug was crystallized. The solid product was filtered using a Buckner funnel under vacuum, and washed thoroughly with hexane. The product was finally crystallized in ethanol and the crystallized product was washed with hexane and dried to obtain around 230 g of solid florfenicol butyrate.

Workup

  1. customequipped with a over head stirrer and a drying tube
  2. customA clear solution was obtained in a few minutes
  3. stirringStirring
  4. customthe florfenicol butyrate pro-drug was crystallized
  5. filtrationThe solid product was filtered
  6. washwashed thoroughly with hexane
  7. customThe product was finally crystallized in ethanol
  8. washthe crystallized product was washed with hexane
  9. customdried

Sources & evidence

ORD record
ord-82ea8eaf7e6f422aaaad937db2a7df1b
Source dataset
uspto-grants-2010_08
Patent number
US07786167B2

Reaction notes

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