Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | p-Toluenesulfonic acid | HCID 6101 | — |
| Reactant | HCID 68470341 | HCID 68470341 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Florfenicol | HCID 114811 | — |
Reaction Steps
(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).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07786329B2 |
|---|
| Source dataset | uspto-grants-2010_08 |
|---|
| ORD ID | ord-99953e722d6c4099858c77f508493564 |
|---|
| Source note | uspto-grants-2010_08 |
|---|
