p-Toluenesulfonic acid → HCID 10834640, Verbindung

HRID 419760Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 419760
[OH:1][C@@H:2]([C@@H:18]1[CH2:22][O:21]C(C)(C)[N:19]1[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:3]#[C:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>CO>[OH:21][CH2:22][C@H:18]([NH:19][C:25](=[O:26])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[C@H:2]([OH:1])[C:3]#[C:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acid2×HCID 516892Sodium BicarbonateHCID 10694286HCID 10694286, Verbindung

Produkt 1

HCID 10834640HCID 10834640, VerbindungAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

The (S)-tert-butyl 4-((R)-1-hydroxy-2-hexadecynyl)-2,2-dimethyloxazolidine-3-carboxylate) (100 mg, 0.23 mmol) obtained in the above-described reaction was dissolved in methanol (4.4 ml); p-toluenesulfonic acid (0.8 mg, 4.6 μmol) was added to the solution, and the mixture was stirred at room temperature for 12 hours. P-toluenesulfonic acid (0.8 mg, 4.6 μmol) was added to this reaction mixture, stirred for 6 hours, heated to 60° C., and further stirred for 2 hours. Saturated sodium hydrogen carbonate was added to this reaction mixture, and the reaction was stopped; the mixture was subsequently extracted with ethyl acetate, and the organic layer was dried and filtered. The resulting filtrate was purified by column chromatography to produce tert-butyl (2S,3R)-1,3-dihydroxyoctadec-4-yn-2-ylcarbamate (85 mg, 93% yield).

Aufarbeitung

  1. stirringstirred for 6 hours
  2. temperatureheated to 60° C.
  3. stirringfurther stirred for 2 hours
  4. extractionthe mixture was subsequently extracted with ethyl acetate
  5. customthe organic layer was dried
  6. filtrationfiltered
  7. customThe resulting filtrate was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c626e4c342b9434fa7f1e48f32104d25
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093395B2

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