Hydrochloric Acid → 2-(2-Ethoxycarbonylfuran-5-yl-methyl)-5-methanesulfonylindole

HRID 1814123Notes

Reaction equation

HRID 1814123 reaction equation
C1(S([N:10]2[C:18]3[C:13](=[CH:14][C:15]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:16][CH:17]=3)[CH:12]=[C:11]2[CH2:23][C:24]2[O:28][C:27]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:26][CH:25]=2)(=O)=O)C=CC=CC=1.[OH-].[K+].Cl>C(O)C>[CH2:32]([O:31][C:29]([C:27]1[O:28][C:24]([CH2:23][C:11]2[NH:10][C:18]3[C:13]([CH:12]=2)=[CH:14][C:15]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:16][CH:17]=3)=[CH:25][CH:26]=1)=[O:30])[CH3:33]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 225044421-Benzenesulfonyl-2-(2-ethoxycarbonylfuran-5-yl-methyl)-5-methanesulfonylindole

Product 1

HCID 225044502-(2-Ethoxycarbonylfuran-5-yl-methyl)-5-methanesulfonylindoleYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
22.5 °C

Procedure

To a solution of the compound obtained in Example 30 (4) (0.1722 g) in ethanol (14 ml), potassium hydroxide (0.047 g) was added and the mixture was stirred at 15 to 30° C. for 30 minutes. To the mixture was added 10% aqueous hydrochloric acid solution, and the mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was separated using silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain 0.0748 g of the desired product.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was separated

Sources & evidence

ORD record
ord-c78b302e78524fb2976393a5ab0470ad
Source dataset
uspto-grants-2005_04
Patent number
US06875770B2

Reaction notes

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