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

HRID 1761160Notes

Reaction equation

HRID 1761160 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-4cfacab08d234f1cbc1964e5aef03e79
Source dataset
uspto-grants-2005_01
Patent number
US06846835B2

Reaction notes

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