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

HRID 553225Notes

Reaction equation

HRID 553225 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+].[NH:24]1[CH2:27][CH:26]([OH:28])[CH2:25]1>COCCOC.O.CN(C)C=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:24]3[CH2:27][CH:26]([OH:28])[CH2:25]3)=[O:17])=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 15142903-HydroxyazetidineHCID 219900803-(2-(1-Benzothiophen-5-yl)ethoxy)propionic acid

Product 1

HCID 219900491-(3-(2-(1-Benzothiophen-5-yl)ethoxy)propionyl)azetidin-3-olYield 90.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

In 15 mL of 1,2-dimethoxyethane was dissolved 10.0 g of 3-(2-(1-benzothiophen-5-yl)ethoxy)propionic acid. Thereto were added 0.1 mL of N,N-dimethylformamide and 5.23 g of thionyl chloride, which was then stirred at room temperature for 1.5 hours. This reaction solution was dropwise added to a mixed solution of 50 mL of water, 7.19 g of sodium hydroxide and 7.69 g of 3-azetidinol 1/2 tartrate at 5 to 15° C., which was then stirred at same temperature for 2 hours. Thereto was added 90 mL of water. The precipitate was collected by filtration to provide 11.0 g of 1-(3-(2-(1-benzothiophen-5-yl)ethoxy)propionyl)azetidin-3-ol as white solid form.

Workup

  1. stirringwhich was then stirred at same temperature for 2 hours
  2. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-fefcee55b24b4d368570665f6ba83c6a
Source dataset
uspto-grants-2011_05
Patent number
US07951963B2

Reaction notes

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