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

HRID 1432272
Notes
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Reaction equation

HRID 1432272 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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-methanesulfonylindole

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=0.1:1) to obtain 0.07.48 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-645d93fef46149709b17645d0aa43247
Source dataset
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07612070B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes