4-Methoxybenzenesulfonyl chloride → 1,3-Dibenzyl-8-(4-methoxy-benzenesulfonyl)-1,4,8-triazaspiro[4,5]decan-2-one

HRID 227259Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 227259
C(N(CC)CC)C.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1.[CH2:20]([N:27]1[C:31]2([CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[NH:30][CH:29]([CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:28]1=[O:44])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[CH2:20]([N:27]1[C:31]2([CH2:32][CH2:33][N:34]([S:16]([C:13]3[CH:14]=[CH:15][C:10]([O:9][CH3:8])=[CH:11][CH:12]=3)(=[O:18])=[O:17])[CH2:35][CH2:36]2)[NH:30][CH:29]([CH2:37][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:28]1=[O:44])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

6

Edukt 4

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 688379421,3-Dibenzyl-1,4,8-triazaspiro[4,5]decan-2-one

Produkt 1

HCID 461430981,3-Dibenzyl-8-(4-methoxy-benzenesulfonyl)-1,4,8-triazaspiro[4,5]decan-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Triethylamine (0.12 ml, 0.89 mmol) and subsequently 4-methoxybenzenesulfonyl chloride (308 mg, 1.49 mmol) were added to a solution of 1,3-dibenzyl-1,4,8-triaza-spiro[4,5]decan-2-one (249 mg, 0.75 mmol) in CH2Cl2 (6.7 ml) with stirring under a blanket of nitrogen at RT. The reaction mixture was stirred overnight. The organic phase was rendered alkaline using saturated aqueous sodium carbonate solution (20 ml), and the aqueous phase was extracted with CH2Cl2 (15 ml). The combined organic phases were dried over Na2SO4. After filtration, removal of the solvent, and column chromatography, the desired product 1,3-dibenzyl-8-(4-methoxy-benzenesulfonyl)-1,4,8-triazaspiro[4,5]decan-2-one was obtained in a yield of 301 mg (79% of theory).

Aufarbeitung

  1. stirringThe reaction mixture was stirred overnight
  2. extractionthe aqueous phase was extracted with CH2Cl2 (15 ml)
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. filtrationAfter filtration, removal of the solvent, and column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-15721f48f09a4486a287ca758628c622
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560468B2

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