Methanol → HCID 58237102, compound

HRID 1188950Notes

Reaction equation

HRID 1188950 reaction equation
CS([O:5][C:6]1[CH:7]=[C:8]([O:20][C:21]2[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=2)[CH:9]=[C:10]2[C:14]=1[NH:13][C:12]([C:15]([O:17]CC)=[O:16])=[CH:11]2)(=O)=O.O1CCCC1.CO.[OH-].[K+]>O>[OH:5][C:6]1[CH:7]=[C:8]([O:20][C:21]2[CH:22]=[CH:23][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:25][CH:26]=2)[CH:9]=[C:10]2[C:14]=1[NH:13][C:12]([C:15]([OH:17])=[O:16])=[CH:11]2

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 58237067HCID 58237067, compound

Product 1

HCID 58237102HCID 58237102, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of ethyl 7-[(methylsulfonyl)oxy]-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylate (2.81 g), tetrahydrofuran (30 mL) and methanol (20 mL) was added a solution of potassium hydroxide (85%, 1.8 g) in water (20 mL). The mixture was stirred at room temperature for 15 h and then partitioned between ethyl acetate and aqueous citric acid solution. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated to give a light brown solid, which was washed with ethyl acetate-hexane to give the title compound (2.12 g, 98%) as a light orange solid.

Workup

  1. custompartitioned between ethyl acetate and aqueous citric acid solution
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a light brown solid, which
  7. washwas washed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-ff51a08a475c40348f9187e33de3a590
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

Loading…