Methyl dichloroacetate → Florfenicol

HRID 1246247Notes

Reaction equation

HRID 1246247 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].C(N(CC)CC)C>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

5

Reactant 3

HCID 8315Methyl dichloroacetateHCID 8471TriethylamineHCID 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 triethylamine (2.05 g, 0.02 mole) and stirred at room temperature for 18 hours. After completion of reaction, methanol was distilled off from the 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 title compound having purity 99.20% by HPLC.

Workup

  1. distillationwas distilled off from the reaction mass, toluene (25 ml) and water (5 ml)
  2. additionwere added
  3. customThe product thus precipitated
  4. filtrationwas filtered
  5. washwashed with methylene chloride (20 ml)
  6. customcrystallized from 2-propanol/water (5:1)

Sources & evidence

ORD record
ord-eb0de7236695484f97bcc55f37d2d047
Source dataset
uspto-grants-2006_10
Patent number
US07126005B2

Reaction notes

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