Water → Ethyl 9-[N-(2-chloro-4-fluorophenyl)sulfamoyl]-3,3-bis(hydroxymethyl)-1,5-dioxaspiro[5.5]undec-7-ene-8-carboxylate

HRID 2191157Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2191157
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([CH:13]1[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][C:16]([O:26][CH3:27])([O:24][CH3:25])[CH2:15][CH2:14]1)(=[O:12])=[O:11].C[Si](C)(C)[O:30][CH2:31][C:32](CO[Si](C)(C)C)(CO[Si](C)(C)C)[CH2:33][O:34][Si](C)(C)C.O>ClCCl.FC(F)(F)S(O[Si](C)(C)C)(=O)=O>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([CH:13]1[CH2:14][CH2:15][C:16]2([O:24][CH2:25][C:32]([CH2:33][OH:34])([CH2:31][OH:30])[CH2:27][O:26]2)[CH:17]=[C:18]1[C:19]([O:21][CH2:22][CH3:23])=[O:20])(=[O:11])=[O:12]

Komponenten

6

Edukt 3

HCID 962WaterHCID 5294792,2,8,8-Tetramethyl-5,5-bis(((trimethylsilyl)oxy)methyl)-3,7-dioxa-2,8-disilanonaneHCID 67192731Ethyl 6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]-3,3-dimethoxy-1-cyclohexene-1-carboxylate

Produkt 1

HCID 16659749Ethyl 9-[N-(2-chloro-4-fluorophenyl)sulfamoyl]-3,3-bis(hydroxymethyl)-1,5-dioxaspiro[5.5]undec-7-ene-8-carboxylateAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 65367Trimethylsilyl triflateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

500 mg (1.19 mmol) of ethyl 6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]-3,3-dimethoxy-1-cyclohexene-1-carboxylate obtained in Example (16a) and 1.0 g (2.38 mmol) of 1,3-bis[(trimethylsilyl)oxy]-2,2-bis[(trimethylsilyl)oxy]methylpropane were dissolved in 10 ml dichloromethane and 10 μl (0.06 mmol) of trimethylsilyl trifluoromethanesulfonate was added thereto with stirring under ice-cooling, followed by stirring for 2 hours at the same temperature. Water was added to the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was subjected to silica gel column chromatography (solvent; ethyl acetate alone) to give 510 mg of the title compound as an amorphous substance (yield: 87%).

Aufarbeitung

  1. temperaturecooling
  2. stirringby stirring for 2 hours at the same temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationfollowed by concentration under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b3b358578f2c481b9db946f2639490f3
Quelldatensatz
uspto-grants-2012_12
Patentnummer
USRE043858E1

Notizen zur Reaktion

Wird geladen…