Potassium Fluoride → (5S)-5-{[(4-Ethynyl-3,6-dihydropyridin-1(2H)-yl)sulfonyl]methyl}-5-methylimidazolidine-2,4-dione

HRID 1669654Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1669654
[CH3:1][C@:2]1([CH2:9][S:10]([N:13]2[CH2:18][CH:17]=[C:16]([C:19]#[C:20][Si](C)(C)C)[CH2:15][CH2:14]2)(=[O:12])=[O:11])[NH:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].[F-].[K+]>CO>[C:19]([C:16]1[CH2:17][CH2:18][N:13]([S:10]([CH2:9][C@@:2]2([CH3:1])[NH:6][C:5](=[O:7])[NH:4][C:3]2=[O:8])(=[O:12])=[O:11])[CH2:14][CH:15]=1)#[CH:20]

Komponenten

4

Edukt 2

HCID 522689Potassium FluorideHCID 67351634(5S)-5-Methyl-5-({[4-[(trimethylsilyl)ethynyl]-3,6-dihydropyridin-1(2H)-yl]sulfonyl}methyl)imidazolidine-2,4-dione

Produkt 1

HCID 86642354(5S)-5-{[(4-Ethynyl-3,6-dihydropyridin-1(2H)-yl)sulfonyl]methyl}-5-methylimidazolidine-2,4-dioneAusbeute 101,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

(5S)-5-Methyl-5-({[4-[(trimethylsilyl)ethynyl]-3,6-dihydropyridin-1(2H) -yl]sulfonyl}methyl)imidazolidine-2,4-dione (2.27 g, 6.0 mmol) and potassium fluoride (1.07 g, 18.4 mmol) were stirred overnight at room temperature in methanol (50 mL). The solvent was evaporated off, the residue dissolved in EtOAc, washed with water followed by brine, dried (sodium sulphate) and evaporated. The residue was purified by column chromatography eluting with iso-hexane/EtOAc 1:1 to give a solid product (1.81 g).

Aufarbeitung

  1. customThe solvent was evaporated off
  2. dissolutionthe residue dissolved in EtOAc
  3. washwashed with water
  4. dry with materialdried (sodium sulphate)
  5. customevaporated
  6. customThe residue was purified by column chromatography
  7. washeluting with iso-hexane/EtOAc 1:1

Quellen und Nachweise

ORD-Eintrag
ord-038dc48a57cb45d3b34ee99b05e3fd28
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989620B2

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