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Hydrochloric Acid → HCID 178464526, Verbindung

HRID 926032
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 926032
[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]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 5

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

Produkt 1

HCID 178464526HCID 178464526, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-1673740f3c324c4881c9b148a0bfd2c5
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09284295B2

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