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Hydrochloric Acid → [3-(3-Benzenesulfonylthiophen-2-ylmethyl)-5-chloro-2-methylindol-1-yl]acetic acid

HRID 1944455
Notes
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Reaction equation

HRID 1944455 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[C:7]([CH2:15][C:16]2[S:17][CH:18]=[CH:19][C:20]=2[S:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:23])=[O:22])=[C:6]1[CH3:30].[OH-].[Li+].Cl>O1CCCC1>[C:24]1([S:21]([C:20]2[CH:19]=[CH:18][S:17][C:16]=2[CH2:15][C:7]2[C:8]3[C:13](=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=3)[N:5]([CH2:4][C:3]([OH:31])=[O:2])[C:6]=2[CH3:30])(=[O:23])=[O:22])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67044072[3-(3-Benzenesulfonylthiophen-2-ylmethyl)-5-chloro-2-methylindol-1-yl]acetic acid methyl ester

Product 1

HCID 58201246[3-(3-Benzenesulfonylthiophen-2-ylmethyl)-5-chloro-2-methylindol-1-yl]acetic acidYield 85.5%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

A mixture of [3-(3-benzenesulfonylthiophen-2-ylmethyl)-5-chloro-2-methylindol-1-yl]acetic acid methyl ester (0.47 g), 1.0 M aqueous lithium hydroxide solution (2.0 mL) and tetrahydrofuran (2.0 mL) was stirred at room temperature for 1 hour. The mixture was acidified with 1.0 M aqueous hydrochloric acid solution and extracted with ethyl acetate. The combined organic extract was dried using a phase separation cartridge and concentrated under reduced pressure. The residue was purified by crystallisation from a mixture of pentane and ethyl acetate to afford the title compound as a white powder (0.39 g).

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe combined organic extract
  3. customwas dried
  4. customa phase separation cartridge
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by crystallisation from a mixture of pentane and ethyl acetate

Sources & evidence

ORD record
ord-6a1c46e5090848c18265bf3d18dd3f96
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08394836B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes