1-Bromo-2-methylpropane → 2-(2-Methyl-propane-1-sulfonylmethyl)-4-morpholin-4-yl-4-oxo-butyric acid

HRID 1830153

Reaktionsgleichung

Reaktionsgleichung von HRID 1830153
[N:1]1([C:7](=[O:24])[CH2:8][CH:9]([CH2:13][S:14]([CH2:17][C:18]2[CH:23]=CC=C[CH:19]=2)(=[O:16])=[O:15])[C:10]([OH:12])=[O:11])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[OH-].[Na+].BrCC(C)C.OOS([O-])=O.[K+]>CCO.O>[CH3:19][CH:18]([CH3:23])[CH2:17][S:14]([CH2:13][CH:9]([CH2:8][C:7]([N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)=[O:24])[C:10]([OH:12])=[O:11])(=[O:15])=[O:16]

Komponenten

7

Edukt 4

HCID 65551-Bromo-2-methylpropaneHCID 14798Sodium HydroxideHCID 22053987HCID 22053987, VerbindungHCID 23707502Potassium hydroxy sulfite

Produkt 1

HCID 115659842-(2-Methyl-propane-1-sulfonylmethyl)-4-morpholin-4-yl-4-oxo-butyric acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

4-Morpholin-4-yl-4-oxo-2-benzylsulfonylmethyl-butyric acid (10.90 g, 40.15 mmol) was dissolved in 100 mL dry EtOH and set to stir at room temperature. NaOH pellets (4.81 g, 120.45 mmol) were added in one portion, and the reaction mixture was allowed to stir for 10 minutes. 1-Bromo-2-methyl propane (5.0 g, 36.49 mmol) was then added, and the reaction mixture was allowed to stir at ambient temperature for 20 hours. Upon completion (LCMS), the reaction mixture was diluted with water and the pH was lowered to ˜pH2. The reaction mixture was then washed 3× with EtOAc. The organic phase was concentrated in vacuo and then diluted with 200 mL aqueous MeOH. Oxone (10.02 g, 14.57 mmol) was added in one portion and the reaction was stirred at room temperature for 4 hours. Conversion of sulfide to sulfone was monitored via LCMS. Upon completion, reaction was quenched by the addition of sodium thiosulfate. Salts were filtered, and the reaction mixture was washed 3× with ethyl acetate and dried over sodium sulfate. The organics were evaporated by vacuum under reduced pressure. Product was purified via HPLC. Yield: 1.1 g, 23.1%. m/z (LCMS) M+ 322.01, Rf=2.03. δH 12.6 (1H, br s), 3.5 (4H, m), 3.5 (1H, m), 3.4 (4H, m), 3.25 (2H, d), 3.0 (2H, m), 2.9 (2H, d), 2.4 (1H, m), 1.3 (6H, d d).

Aufarbeitung

  1. additionwere added in one portion
  2. stirringto stir for 10 minutes
  3. stirringto stir at ambient temperature for 20 hours
  4. washThe reaction mixture was then washed 3× with EtOAc
  5. concentrationThe organic phase was concentrated in vacuo
  6. additiondiluted with 200 mL aqueous MeOH
  7. stirringthe reaction was stirred at room temperature for 4 hours
  8. customUpon completion, reaction
  9. customwas quenched by the addition of sodium thiosulfate
  10. filtrationSalts were filtered
  11. washthe reaction mixture was washed 3× with ethyl acetate
  12. dry with materialdried over sodium sulfate
  13. customThe organics were evaporated by vacuum under reduced pressure
  14. customProduct was purified via HPLC

Quellen und Nachweise

ORD-Eintrag
ord-8cc58baaece44623b4184d194b200623
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07064123B1

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