Hydrochloric Acid → 4-(3-Cyclohexyl-indole-1-sulfonyl)-benzoic acid

HRID 737010Notes

Reaction equation

HRID 737010 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:30])[C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=[CH:16]2)(=[O:14])=[O:13])=[CH:8][CH:7]=1.Cl>C1COCC1.CO.CCOC(C)=O>[CH:24]1([C:17]2[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:15]([S:12]([C:9]3[CH:10]=[CH:11][C:6]([C:5]([OH:30])=[O:4])=[CH:7][CH:8]=3)(=[O:14])=[O:13])[CH:16]=2)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 589752204-(3-Cyclohexyl-indole-1-sulfonyl)-benzoic acid methyl ester

Product 1

HCID 589752174-(3-Cyclohexyl-indole-1-sulfonyl)-benzoic acidYield 86.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add 5N sodium hydroxide (1.17 ml, 3 eq) to a solution of 4-(3-Cyclohexyl-indole-1-sulfonyl)-benzoic acid methyl ester (775 mg, 1.95 mmol, 1 eq) dissolve in a mixture of 10 ml THF and 5 ml MeOH. Stir for 1.5 hours. Remove solvent on rotovap and add 1 N HCl. Dissolve the solid that crashes out of solution in EtOAc. Extract product into organics, separate organics, dry over MgSO4, and concentrate on rotovap to give 4-(3-Cyclohexyl-indole-1-sulfonyl)-benzoic acid (646 mg, 86% yield) as a white solid.

Workup

  1. customExtract product into organics, separate organics
  2. dry with materialdry over MgSO4
  3. concentrationconcentrate on rotovap

Sources & evidence

ORD record
ord-f67840dfdb91438c9050fd2cebd9aec7
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

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