Water → HCID 68543002, compound

HRID 2243510Notes

Reaction equation

HRID 2243510 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]2[C:6]3[S:11][C:10]([C:12]#[N:13])=[C:9]([O:14][CH2:15][C:16]([O:18]C)=[O:17])[C:7]=3[S:8][C:4]=2[CH:3]=1.[OH-].[K+].O>C1COCC1.CO>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]2[C:6]3[S:11][C:10]([C:12]#[N:13])=[C:9]([O:14][CH2:15][C:16]([OH:18])=[O:17])[C:7]=3[S:8][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 86605576HCID 86605576, compound

Product 1

HCID 68543002HCID 68543002, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl [(6-chloro-2-cyanothieno[3,2-b][1]benzothien-3-yl)oxy]acetate (100 mg, 0.3 mmol) and potassium hydroxide (39 mg, 2 eq) in THF (2 mL), MeOH, (1 mL), and water (1 mL) was stirred at room temperature for 4h. The solvents were removed by evaporation, and the resulting oil was acidified with aq. hydrochloric acid, filtered, washed with water and dried in a vacuum oven overnight to provide [(6-chloro-2-cyanothieno[3,2-b][1]benzothien-3-yl)oxy]acetic acid (72 mg). This sample was further purified by reverse phase HPLC to provide 23 mg of the product.

Workup

  1. customThe solvents were removed by evaporation
  2. filtrationfiltered
  3. washwashed with water
  4. customdried in a vacuum oven overnight

Sources & evidence

ORD record
ord-414e4593ad254069b53abe63146b0474
Source dataset
uspto-grants-2010_03
Patent number
US07674822B2

Reaction notes

Loading…