Reacción #595074

ord-99953e722d6c4099858c77f508493564

Ecuación de reacción

CC1(C)O[C@H](c2ccc(S(C)(=O)=O)cc2)[C@@H](CF)N1C(=O)C(Cl)Cl
(4S,5R)-3-dichloroacetyl-2,2-dimethyl-4-fluoromethyl-5-[4-(methylsulfonyl)phenyl]-1,3-oxazolidine
O
water
Cc1ccc(S(=O)(=O)O)cc1
p-toluene sulfonic acid
→
CS(=O)(=O)c1ccc([C@@H](O)[C@@H](CF)NC(=O)C(Cl)Cl)cc1
(1R,2S)-2-dichloroacetamido-3-fluoro-1-[4-(methylsulfonyl)phenyl]-1-propanol

Reactantes

CC1(C)O[C@H](c2ccc(S(C)(=O)=O)cc2)[C@@H](CF)N1C(=O)C(Cl)Cl
(4S,5R)-3-dichloroacetyl-2,2-dimethyl-4-fluoromethyl-5-[4-(methylsulfonyl)phenyl]-1,3-oxazolidine
O
water
Cc1ccc(S(=O)(=O)O)cc1
p-toluene sulfonic acid

Reactivos

Ninguno

Disolventes

ClCCl
methylene chloride

Condiciones de reacción

Temperatura
22.5°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroRemoval of the methylene chloride
  2. 2
    workup.DISTILLATIONby distillation
  3. 3
    Otroprecipitates the product
  4. 4
    FiltraciónFiltration
  5. 5
    Lavadowashing with water (100 mL) and toluene (100 mL)
  6. 6
    Otrothen drying

Procedimiento

(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).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07786329B2uspto-grants-2010_08