Potassium Hydroxide → Indeglitazar

HRID 2100435Notes

Reaction equation

HRID 2100435 reaction equation
C[O:2][C:3](=[O:28])[CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]([S:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH:7]=1.[OH-].[K+]>O1CCCC1>[CH3:16][O:15][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]([S:17]([C:20]1[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=1)(=[O:19])=[O:18])[CH:7]=[C:6]2[CH2:5][CH2:4][C:3]([OH:28])=[O:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 588431163-[5-Methoxy-1-(4-methoxy-benzenesulfonyl)-1H-indol-3-yl]-propionic acid methyl ester

Product 1

HCID 11395145Indeglitazar

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the methyl ester 5 (830 mg, 2.06 mmol) in tetrahydrofuran (15 mL) was added an aqueous solution of potassium hydroxide (5 mL of 1M) and stirred at room temperature for 5 h. The acid 1 was isolated by neutralizing the reaction mixture by aqueous hydrochloric acid, extracting the product with ethyl acetate, drying over anhydrous magnesium sulfate, evaporating under reduced pressure, and purifying using flash chromatography with 5% methanol in dichloromethane to afford a white solid (697.5 mg, 91%; M-1=373.1).

Sources & evidence

ORD record
ord-f03f764fddb24e3ca6bafd1f87f8c564
Source dataset
uspto-grants-2009_08
Patent number
US07572806B2

Reaction notes

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