Dichloromethane → Florfenicol

HRID 1246249Notes

Reaction equation

HRID 1246249 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].C(Cl)Cl.[Cl:20][CH:21]([Cl:25])[C:22](Cl)=[O:23]>O>[Cl:20][CH:21]([Cl:25])[C:22]([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:23]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6593Dichloroacetyl chlorideHCID 156406Florfenicol amine

Product 1

HCID 114811FlorfenicolYield 69.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of (1R,2S)-1-[4-(methylsulfonyl)phenyl]-2-amino-3-fluoro-1-propanol (5 g, 0.02 moles) in methylene chloride (100 ml) triethylamine (3.0 g, 0.03 mole) and dichloro acetyl chloride (3.6 g; 0.025 mole) were added at 10–15° C. After completion of reaction in 30 minutes, water (10 ml) was added and layers were separated. Solvent 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 ethanol/water (4:1) to give 5 g of the title compound with purity 99.5% by HPLC.

Workup

  1. customAfter completion of reaction in 30 minutes
  2. customlayers were separated
  3. distillationSolvent was 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 ethanol/water (4:1)

Sources & evidence

ORD record
ord-87ff2c206d8f467bbd88c3780688ea79
Source dataset
uspto-grants-2006_10
Patent number
US07126005B2

Reaction notes

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