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Potassium Hydroxide → 5-Cyclopropyl-2-(4-fluorophenyl)-6-((methylsulfonyl)amino)-3-benzofurancarboxylic acid

HRID 2272288
Notes
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Reaction equation

HRID 2272288 reaction equation
[CH3:1][S:2]([N:5](S(C)(=O)=O)[C:6]1[C:25]([CH:26]2[CH2:28][CH2:27]2)=[CH:24][C:9]2[C:10]([C:20]([O:22]C)=[O:21])=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[O:12][C:8]=2[CH:7]=1)(=[O:4])=[O:3].[OH-].[K+]>C(O)C.O>[CH:26]1([C:25]2[C:6]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:7][C:8]3[O:12][C:11]([C:13]4[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=4)=[C:10]([C:20]([OH:22])=[O:21])[C:9]=3[CH:24]=2)[CH2:27][CH2:28]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 67355848Methyl 6-[bis(methylsulfonyl)amino]-5-cyclopropyl-2-(4-fluorophenyl)-1-benzofuran-3-carboxylate

Product 1

HCID 673529905-Cyclopropyl-2-(4-fluorophenyl)-6-((methylsulfonyl)amino)-3-benzofurancarboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962Water
Solvent

Procedure

A suspension of methyl 6-[bis(methylsulfonyl)amino]-5-cyclopropyl-2-(4-fluorophenyl)-1-benzofuran-3-carboxylate (2.88 g, 5.98 mmol) in ethanol (50 mL) and water (25 mL) was treated with potassium hydroxide (6.71 g, 120 mmol) and heated at reflux for 1 hour (the suspension went into solution upon heating). The reaction was concentrated under vacuum, water (100 mL) was added and the solution acidified with 2M HCl (50 mL). The resulting precipitate was filtered, washed with 0.5 M HCl, then dissolved in methanol. This solution was evaporated to dryness and azeotroped twice with toluene to give 5-Cyclopropyl-2-(4-fluorophenyl)-6-[(methylsulfonyl)amino]-1-benzofuran-3-carboxylic acid. LCMS (m/z, ES+)=390 (M+H+).

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hour (the suspension
  3. temperatureupon heating)
  4. concentrationThe reaction was concentrated under vacuum, water (100 mL)
  5. additionwas added
  6. filtrationThe resulting precipitate was filtered
  7. washwashed with 0.5 M HCl
  8. dissolutiondissolved in methanol
  9. customThis solution was evaporated to dryness
  10. customazeotroped twice with toluene

Sources & evidence

ORD record
ord-223f41fa53b24517baba40a5ff2968c1
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09119868B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes