Bis(2-chloroethyl) ether → HCID 69080139, compound

HRID 458735Notes

Reaction equation

HRID 458735 reaction equation
[F:1][C:2]1([F:23])[CH2:6][CH2:5][C@@H:4]([C@@:7]([OH:22])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]([O:10][C@@H:11]2[CH2:15][CH2:14][NH:13][CH2:12]2)=[O:9])[CH2:3]1.[Cl:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29]Cl>C(#N)C>[Cl-:24].[F:23][C:2]1([F:1])[CH2:6][CH2:5][C@@H:4]([C@@:7]([OH:22])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]([O:10][C@@H:11]2[CH2:15][CH2:14][N+:13]3([CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[CH2:12]2)=[O:9])[CH2:3]1

Participants

4

Reactant 2

HCID 8115Bis(2-chloroethyl) etherHCID 69768170HCID 69768170, compound

Product 1

HCID 69080139HCID 69080139, compoundYield 19.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To an acetonitrile solution containing 11 mg of (3R)-pyrrolidin-3-yl (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoate, 30 mg of 1-chloro-2-(2-chloroethoxy)ethane was added at room temperature, followed by 12 hours' heating under reflux. Distilling the solvent off under reduced pressure, the residue was purified on preparative thin layer chromatography (Aluminiumoxide™60F254, Art5713 (Merck), chloroform/methanol=10/1) to provide 2.8 mg of the title compound as a colorless oily substance.

Workup

  1. additionwas added at room temperature
  2. temperature' heating
  3. temperatureunder reflux
  4. distillationDistilling the solvent off under reduced pressure
  5. customthe residue was purified on preparative thin layer chromatography (Aluminiumoxide™60F254, Art5713 (Merck), chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-bfccbd47a2494f68b295b31ee53a4dec
Source dataset
uspto-grants-2007_03
Patent number
US07192969B2

Reaction notes

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