Sodium Hydroxide → 1-(3-(2-(1-Benzothiophen-5-yl)ethoxy)propionyl)azetidin-3-ol

HRID 553226Notes

Reaction equation

HRID 553226 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][O:12][CH2:13][CH2:14][C:15]([OH:17])=O)=[CH:9][C:4]=2[CH:3]=[CH:2]1.S(Cl)(Cl)=O.[OH-].[Na+].Cl.[NH:25]1[CH2:28][CH:27]([OH:29])[CH2:26]1>COCCOC.O>[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][O:12][CH2:13][CH2:14][C:15]([N:25]3[CH2:28][CH:27]([OH:29])[CH2:26]3)=[O:17])=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 27592903-Hydroxyazetidine hydrochlorideHCID 219900803-(2-(1-Benzothiophen-5-yl)ethoxy)propionic acid

Product 1

HCID 219900491-(3-(2-(1-Benzothiophen-5-yl)ethoxy)propionyl)azetidin-3-olYield 92.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
7.5 °C

Procedure

In 75 mL of 1,2-dimethoxyethane was dissolved 50.0 g of 3-(2-(1-benzothiophen-5-yl)ethoxy)propionic acid. Thereto was added 26.1 g of thionyl chloride, which was then refluxed for 2 hours. After cooling, this reaction solution was dropwise added to a mixed solution of 125 mL of water, 20.0 g of sodium hydroxide and 25.2 g of 3-azetidinol hydrochloride at −5 to 10° C., which was then stirred at 0 to 15° C. for 30 minutes. Thereto was added 75 mL of water, which was heated to 40° C. and dissolved. After cooling, the precipitate was collected by filtration to provide 56.5 g of 1-(3-(2-(1-benzothiophen-5-yl)ethoxy)propionyl)azetidin-3-ol as white solid form.

Workup

  1. temperaturewas then refluxed for 2 hours
  2. temperatureAfter cooling
  3. temperaturewas heated to 40° C.
  4. dissolutiondissolved
  5. temperatureAfter cooling
  6. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-d86a366c3a06404e8617a35a8fdfa0ba
Source dataset
uspto-grants-2011_05
Patent number
US07951963B2

Reaction notes

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