Methanol → HCID 59252803, compound

HRID 563385Notes

Reaction equation

HRID 563385 reaction equation
CN(C)C([N:5]1[C:13]2[C:8](=[CH:9][C:10]([CH:14]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:15]([CH3:21])([CH3:20])[C:16]([O:18]C)=[O:17])=[CH:11][CH:12]=2)[CH:7]=[CH:6]1)=O.[OH-].[Na+].CO>CS(C)=O>[NH:5]1[C:13]2[C:8](=[CH:9][C:10]([CH:14]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:15]([CH3:21])([CH3:20])[C:16]([OH:18])=[O:17])=[CH:11][CH:12]=2)[CH:7]=[CH:6]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 59252823HCID 59252823, compound

Product 1

HCID 59252803HCID 59252803, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methyl 3-(1-(dimethylcarbamoyl)-1H-indol-5-yl)-2,2-dimethyl-3-phenylpropanoate (0.7 g, 2.2 mmol), sodium hydroxide (1M aqueous solution, 18 mL), methanol (5 mL), and dimethylsulfoxide (3 mL) was stirred at 100° C. overnight under argon. The reaction mixture was cooled, washed with diethyl ether (20 mL), acidified with 6M hydrochloric acid aqueous solution, and extracted with ethyl acetate (20 mL). The ethyl acetate extract was washed with brine (20 mL), dried (Na2SO4) and concentrated to give 3-(1H-indol-5-yl)-2,2-dimethyl-3-phenylpropanoic acid (0.58 g, 2.0 mmol, 91% yield) as a syrup and used as such for the subsequent step without further purification.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with diethyl ether (20 mL)
  3. extractionextracted with ethyl acetate (20 mL)
  4. extractionThe ethyl acetate extract
  5. washwas washed with brine (20 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2743a35a081b4b69af3773ff6aa9bae8
Source dataset
uspto-grants-2011_11
Patent number
US08067447B2

Reaction notes

Loading…