Hydrochloric Acid → 3-{[1-(Ethoxycarbonyl)cyclopropyl](isopropyl)sulfamoyl}benzoic acid

HRID 926040Notes

Reaction equation

HRID 926040 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([NH:9][S:10]([C:13]2[CH:14]=[C:15]([CH:25]=[CH:26][CH:27]=2)[C:16]([O:18]CC[Si](C)(C)C)=[O:17])(=[O:12])=[O:11])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH:28](I)([CH3:30])[CH3:29].C(=O)([O-])[O-].[K+].[K+].CCCC[N+](CCCC)(CCCC)CCCC.[F-].Cl>C1COCC1.O.CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1([N:9]([CH:28]([CH3:30])[CH3:29])[S:10]([C:13]2[CH:14]=[C:15]([CH:25]=[CH:26][CH:27]=2)[C:16]([OH:18])=[O:17])(=[O:11])=[O:12])[CH2:7][CH2:8]1)=[O:5])[CH3:2]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 2724141Tetrabutylammonium FluorideHCID 712385892-(Trimethylsilyl)ethyl 3-{[1-(ethoxycarbonyl)cyclopropyl]sulfamoyl}benzoate

Product 1

HCID 682078783-{[1-(Ethoxycarbonyl)cyclopropyl](isopropyl)sulfamoyl}benzoic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
65 °C

Procedure

A mixture of 450 mg of 2-(trimethylsilyl)ethyl 3-{[1-(ethoxycarbonyl)cyclopropyl]sulfamoyl}benzoate, 0.22 mL of isopropyl iodide, 451 mg of potassium carbonate, and 4.5 mL of DMF were stirred at 65° C. overnight. To the reaction mixture was added water, followed by extraction with ethyl acetate. Then, the organic layer was washed with water and saturated brine in this order, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain a pale yellow oily substance. To the obtained oily substance were added a solution of TBAF in THF (1.0 M, 2.0 mL) and 4.5 mL of THF, followed by stirring at room temperature for 2 hours. To the reaction mixture was added 0.2 M hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with 0.2 M hydrochloric acid, water, and saturated brine in this order, and then dried over anhydrous sodium sulfate. The resultant was concentrated under reduced pressure to obtain 319 mg of 3-{[1-(ethoxycarbonyl)cyclopropyl](isopropyl)sulfamoyl}benzoic acid as a colorless oily substance.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThen, the organic layer was washed with water and saturated brine in this order
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto obtain a pale yellow oily substance
  6. stirringby stirring at room temperature for 2 hours
  7. extractionfollowed by extraction with ethyl acetate
  8. washThe organic layer was washed with 0.2 M hydrochloric acid, water, and saturated brine in this order
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationThe resultant was concentrated under reduced pressure

Sources & evidence

ORD record
ord-50f6b9f84a7e487d9c27872ff9cf87e8
Source dataset
uspto-grants-2016_03
Patent number
US09284295B2

Reaction notes

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