Dimethylformamide → HCID 178495951, Verbindung

HRID 1025422

Reaktionsgleichung

Reaktionsgleichung von HRID 1025422
[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](OCC[Si](C)(C)C)=[O:19])(=[O:14])=[O:13])[CH2:7][CH2:6]1)=[O:4].CN(C=[O:34])C.Br[CH2:36][CH2:37][O:38][CH3:39].C(=O)([O-])[O-].[K+].[K+]>O>[CH3:1][O:2][C:3]([C@H:5]1[CH2:6][CH2:7][C@H:8]([N:11]([CH2:36][CH2:37][O:38][CH3:39])[S:12]([C:15]2[CH:16]=[C:17]([CH:27]=[CH:28][CH:29]=2)[C:18]([OH:19])=[O:34])(=[O:13])=[O:14])[CH2:9][CH2:10]1)=[O:4]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 178501248HCID 178501248, Verbindung

Produkt 1

HCID 178495951HCID 178495951, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a mixture of 1.00 g of 2-(trimethylsilyl)ethyl 3-{[trans-4-(methoxycarbonyl)cyclohexyl]sulfamoyl}benzoate and 10 mL of DMF were added 0.63 g of 2-bromoethylmethyl ether and 0.94 g of potassium carbonate at room temperature, followed by stirring at 60° C. overnight. The reaction mixture was cooled to room temperature, and then water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine in this order, and dried over anhydrous sodium sulfate. The resultant was concentrated under reduced pressure, and to a mixture of the obtained residue and 10 mL of THF was added a solution of TBAF in THF (1.0 M, 4.0 mL), followed by stirring at room temperature for 3 hours. A solution of TBAF in THF (1.0 M, 2.0 mL) was further added thereto, followed by stirring at room temperature for 1.5 hours. The reaction mixture was diluted with ethyl acetate, and then washed with 0.2 M hydrochloric acid, water, and saturated brine in this order. The obtained organic layer was dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain 915 mg of 3-{[trans-4-(methoxycarbonyl)cyclohexyl](2-methoxyethyl)sulfamoyl}benzoic acid as a colorless amorphous solid.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine in this order
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe resultant was concentrated under reduced pressure
  6. additionto a mixture of the obtained residue and 10 mL of THF
  7. additionwas added a solution of TBAF in THF (1.0 M, 4.0 mL)
  8. stirringby stirring at room temperature for 3 hours
  9. additionA solution of TBAF in THF (1.0 M, 2.0 mL) was further added
  10. stirringby stirring at room temperature for 1.5 hours
  11. additionThe reaction mixture was diluted with ethyl acetate
  12. washwashed with 0.2 M hydrochloric acid, water, and saturated brine in this order
  13. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  14. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-57838584be7748d2869ff0d708310240
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08729068B2

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