Tetrahydrofuran → HCID 66657892, compound

HRID 420596Notes

Reaction equation

HRID 420596 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][CH:17]2[CH2:21][CH2:20][N:19]([C:22]3[S:23][C:24]4[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:25]=4[N:26]=3)[CH2:18]2)[CH:6]=1.[OH-].[Na+].O1CCCC1>CO>[Cl:31][C:29]1[CH:28]=[CH:27][C:25]2[N:26]=[C:22]([N:19]3[CH2:20][CH2:21][CH:17]([CH2:16][CH2:15][NH:14][CH2:13][CH2:12][O:11][C:7]4[CH:6]=[C:5]([CH2:4][C:3]([OH:32])=[O:2])[CH:10]=[CH:9][CH:8]=4)[CH2:18]3)[S:23][C:24]=2[CH:30]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66657857HCID 66657857, compound

Product 1

HCID 66657892HCID 66657892, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of [3-[2-[[1-(6-chlorobenzothiazole-2-yl)pyrrolidine-3-yl]ethylamino]ethoxy]phenyl]acetic acid methyl ester (101 mg), 2N aqueous sodium hydroxide (0.535 mL), tetrahydrofuran (1 mL) and methanol (0.5 mL) was stirred at room temperature for 1 hour. The reaction solution was concentrated under reduced pressure and extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over sodium sulphate. The solvent was evaporated under reduced pressure and the residue was washed with ethyl acetate/n-hexane to give the title compound (13 mg). Yield: 14%.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulphate
  5. customThe solvent was evaporated under reduced pressure
  6. washthe residue was washed with ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-48dc07cf740b4bc49a4ec76ff70065f1
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

Loading…