Hydrochloric Acid → HCID 178464526, compound

HRID 926032

Reaction equation

HRID 926032 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][S:12]([C:15]2[CH:16]=[C:17]([CH:27]=[CH:28][CH:29]=2)[C:18]([O:20]CC[Si](C)(C)C)=[O:19])(=[O:14])=[O:13])[CH2:7][CH2:6]1)=[O:4].[CH2:30](I)[CH3:31].C(=O)([O-])[O-].[K+].[K+].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl>C1COCC1.O.CN(C=O)C>[CH2:30]([N:11]([C@H:8]1[CH2:9][CH2:10][C@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][CH2:7]1)[S:12]([C:15]1[CH:16]=[C:17]([CH:27]=[CH:28][CH:29]=1)[C:18]([OH:20])=[O:19])(=[O:13])=[O:14])[CH3:31]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 2724141Tetrabutylammonium FluorideHCID 178501248HCID 178501248, compound

Product 1

HCID 178464526HCID 178464526, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
65 °C

Procedure

A mixture of 450 mg of 2-(trimethylsilyl)ethyl 3-{[trans-4-(methoxycarbonyl)cyclohexyl]sulfamoyl}benzoate, 0.15 mL of ethyl iodide, 422 mg of potassium carbonate, and 4.5 mL of DMF was 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 colorless oily substance. To the obtained oily substance were added a solution of tetrabutyl ammonium fluoride (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, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 355 mg of 3-{ethyl[trans-4-(methoxycarbonyl)cyclohexyl]sulfamoyl}benzoic acid as a colorless solid.

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 colorless 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. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1673740f3c324c4881c9b148a0bfd2c5
Source dataset
uspto-grants-2016_03
Patent number
US09284295B2

Linked notes

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