Methyl dichloroacetate → Florfenicol

HRID 1246248Notes

Reaction equation

HRID 1246248 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]([OH:16])[C@H:12]([NH2:15])[CH2:13][F:14])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[Cl:17][CH:18]([Cl:23])[C:19](OC)=[O:20]>CO>[Cl:17][CH:18]([Cl:23])[C:19]([NH:15][C@H:12]([CH2:13][F:14])[C@@H:11]([C:8]1[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:10][CH:9]=1)[OH:16])=[O:20]

Participants

4

Reactant 2

HCID 8315Methyl dichloroacetateHCID 156406Florfenicol amine

Product 1

HCID 114811FlorfenicolYield 69.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of (1R,2S)-1-[4-(methylsulfonyl)phenyl]-2-amino-3-fluoro-1-propanol (5 g, 0.02 moles) in methanol (50 ml) was added methyl dichloroacetate (14.5 g; 0.10 g) and heated to reflux at 60° C. to 65° C. for 18 hours. After completion of reaction, methanol was distilled off from reaction mass, toluene (25 ml) and water (5 ml) were added. The product thus precipitated was filtered, washed with methylene chloride (20 ml) and crystallized from 2-propanol/water (5:1) to give 5 g of Florfenicol with 99% HPLC purity.

Workup

  1. temperatureheated
  2. temperatureto reflux at 60° C. to 65° C. for 18 hours
  3. distillationwas distilled off from reaction mass, toluene (25 ml) and water (5 ml)
  4. additionwere added
  5. customThe product thus precipitated
  6. filtrationwas filtered
  7. washwashed with methylene chloride (20 ml)
  8. customcrystallized from 2-propanol/water (5:1)

Sources & evidence

ORD record
ord-5b281f089bc54cf08a2315c3eb5f397e
Source dataset
uspto-grants-2006_10
Patent number
US07126005B2

Reaction notes

Loading…