Water → Florfenicol

HRID 507892Notes

Reaction equation

HRID 507892 reaction equation
[Cl:1][CH:2]([Cl:24])[C:3]([N:5]1[C@H:9]([CH2:10][F:11])[C@@H:8]([C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=2)[O:7]C1(C)C)=[O:4].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[Cl:24][CH:2]([Cl:1])[C:3]([NH:5][C@H:9]([CH2:10][F:11])[C@@H:8]([C:12]1[CH:13]=[CH:14][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:16][CH:17]=1)[OH:7])=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 68470341HCID 68470341, compound

Product 1

HCID 114811Florfenicol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
22.5 °C

Procedure

(4S,5R)-3-dichloroacetyl-2,2-dimethyl-4-fluoromethyl-5-[4-(methylsulfonyl)phenyl]-1,3-oxazolidine (Compound XIIIa) (60.5 g, 0.1519 moles) selectively hydrolyses in methylene chloride (300 mL) and water (100 mL) containing p-toluene sulfonic acid at 60° C. over several hours. Removal of the methylene chloride by distillation and cooling to 20-25° C. precipitates the product. Filtration, washing with water (100 mL) and toluene (100 mL) then drying yields (1R,2S)-2-dichloroacetamido-3-fluoro-1-[4-(methylsulfonyl)phenyl]-1-propanol (Florfenicol).

Workup

  1. customRemoval of the methylene chloride
  2. distillationby distillation
  3. customprecipitates the product
  4. filtrationFiltration
  5. washwashing with water (100 mL) and toluene (100 mL)
  6. customthen drying

Sources & evidence

ORD record
ord-99953e722d6c4099858c77f508493564
Source dataset
uspto-grants-2010_08
Patent number
US07786329B2

Reaction notes

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