Hydrochloric Acid → [1-(3,4-dichloro-benzenesulfonyl)-5-methoxy-1H-indol-3-ylsulfanyl]-acetic acid

HRID 491860Notes

Reaction equation

HRID 491860 reaction equation
C[O:2][C:3](=[O:28])[CH2:4][S:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]([S:17]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=2)(=[O:19])=[O:18])[CH:7]=1.[OH-].[K+].Cl>C1COCC1>[Cl:27][C:22]1[CH:21]=[C:20]([S:17]([N:8]2[C:9]3[C:14](=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=3)[C:6]([S:5][CH2:4][C:3]([OH:28])=[O:2])=[CH:7]2)(=[O:19])=[O:18])[CH:25]=[CH:24][C:23]=1[Cl:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 57678944HCID 57678944, compound

Product 1

HCID 11676670[1-(3,4-dichloro-benzenesulfonyl)-5-methoxy-1H-indol-3-ylsulfanyl]-acetic acidYield 5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (5-Methoxy-1H-indol-3-ylsulfanyl)-acetic acid methyl ester 26, in THF (4.0 mL) was added an aqueous solution of potassium hydroxide (1.0 mL of 1M) which was stirred at room temperature for 4 h. The acid was neutralized with aqueous HCl, extracted the product with ethyl acetate, dried over anhydrous magnesium sulfate, evaporated under reduced pressure, and purified via trituration with tetrabutyl ethyl ether to afford 27 as a white solid (4.5 mg, 5%). MS(ESI) [M+H−]+=443.95

Workup

  1. extractionextracted the product with ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customevaporated under reduced pressure
  4. custompurified via trituration with tetrabutyl ethyl ether

Sources & evidence

ORD record
ord-6f15ba14661940c8a0811c4a032e3d64
Source dataset
uspto-grants-2009_05
Patent number
US07531568B2

Reaction notes

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