Hydrochloric Acid → 3-{[5-(Methoxycarbonyl)pyridin-2-yl](propyl)sulfamoyl}benzoic acid

HRID 926050Notes

Reaction equation

HRID 926050 reaction equation
[CH2:1]([N:4]([S:15]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([O:26]CC[Si](C)(C)C)=[O:25])[CH:19]=1)(=[O:17])=[O:16])[C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][N:6]=1)[CH2:2][CH3:3].CCCC[N+](CCCC)(CCCC)CCCC.[F-].Cl>C1COCC1>[CH3:12][O:11][C:9]([C:8]1[CH:13]=[CH:14][C:5]([N:4]([CH2:1][CH2:2][CH3:3])[S:15]([C:18]2[CH:19]=[C:20]([CH:21]=[CH:22][CH:23]=2)[C:24]([OH:26])=[O:25])(=[O:16])=[O:17])=[N:6][CH:7]=1)=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2724141Tetrabutylammonium FluorideHCID 71238187Methyl 6-{propyl[(3-{[2-(trimethylsilyl)ethoxy]carbonyl}phenyl)sulfonyl]amino}nicotinate

Product 1

HCID 712387833-{[5-(Methoxycarbonyl)pyridin-2-yl](propyl)sulfamoyl}benzoic acidYield 79.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 175 mg of methyl 6-{propyl[(3-{[2-(trimethylsilyl)ethoxy]carbonyl}phenyl)sulfonyl]amino}nicotinate and 5 mL of THF was added dropwise a solution of TBAF in THF (1 M, 0.750 mL), followed by stirring at room temperature for 4 hours. To the reaction mixture was added 0.1 M hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, and then dried over magnesium sulfate. The solvent was evaporated under reduced pressure and then dried under reduced pressure to obtain 110 mg of 3-{[5-(methoxycarbonyl)pyridin-2-yl](propyl)sulfamoyl}benzoic acid as a colorless powder.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-78e8d6c629e14fd980c9e325c38db832
Source dataset
uspto-grants-2016_03
Patent number
US09284295B2

Reaction notes

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