Water → HCID 14931303, Verbindung

HRID 973993

Reaktionsgleichung

Reaktionsgleichung von HRID 973993
[CH:1]1([C@:7]([OH:17])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([OH:10])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:18][N:19]([CH3:25])[CH2:20][C:21]#[C:22][CH2:23][NH2:24].O>C(Cl)(Cl)Cl>[CH3:18][N:19]([CH3:25])[CH2:20][C:21]#[C:22][CH2:23][NH:24][C:8](=[O:10])[C:7]([CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)([OH:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 777375Cyclohexylphenylglycolic acid, (+)-HCID 12259565HCID 12259565, Verbindung

Produkt 1

HCID 14931303HCID 14931303, VerbindungAusbeute 37,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A mixture of (S)-(+)-2-cyclohexyl-2-hydroxy-2-phenylacetic acid (1.13 g, 80% ee) and N,N'-carbonyldiimidazole (0.77 g) in chloroform (5 ml) was stirred at room temperature for 2 hours. After an addition of 4-dimethylamino-2-butynylamine (0.54 g), the mixture was stirred at the same temperature for an additional hour, then the mixture was poured into water, and extracted with ethyl acetate. The extract was washed with water and the organic layer was extracted with 1N-hydrochloric acid. The acidic solution was adjusted to pH 13 with aqueous solution of sodium hydroxide and extracted with ethyl acetate. The extract was washed with sodium chloride aqueous solution, dried over sodium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of chloroform and methanol (10:1) as an eluent to give (-)-N-(4-dimethylamino-2-butynyl)-2-cyclohexyl-2-hydroxy-2-phenylacetamide (0.60 g, 88% ee).

Aufarbeitung

  1. stirringthe mixture was stirred at the same temperature for an additional hour
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. extractionthe organic layer was extracted with 1N-hydrochloric acid
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with sodium chloride aqueous solution
  7. dry with materialdried over sodium sulfate
  8. customevaporated in vacuo
  9. customThe residue was purified by column chromatography on silica gel with a mixture of chloroform and methanol (10:1) as an eluent

Quellen und Nachweise

ORD-Eintrag
ord-a0ed4e33b64f471db91fd85425548675
Quelldatensatz
uspto-grants-1991_11
Patentnummer
US05066680

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