Dihydroxyacetone → HCID 21075964, Verbindung

HRID 414932

Reaktionsgleichung

Reaktionsgleichung von HRID 414932
C1(N=C=NC2CCCCC2)CCCCC1.[CH3:16][O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[CH:24]=[C:23]([C@H:28]([CH3:32])[C:29]([OH:31])=[O:30])[CH:22]=[CH:21]2.[OH:33][CH2:34][C:35]([CH2:37]O)=[O:36]>CC(C)=O>[CH3:16][O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[CH:24]=[C:23]([C@H:28]([CH3:32])[C:29]([O:31][CH2:37][C:35](=[O:36])[CH2:34][OH:33])=[O:30])[CH:22]=[CH:21]2

Komponenten

5

Edukt 3

HCID 670DihydroxyacetoneHCID 10868DicyclohexylcarbodiimideHCID 156391Naproxen

Produkt 1

HCID 21075964HCID 21075964, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel2×

Versuchsvorschrift

A solution of 1,3-dicyclohexylcarbodiimide (2.84 g, 13.8 mmol) in acetone (40 mL) was added, drop-wise, to a solution of (2S)-2-(6-methoxy(2-naphthyl))propanoic acid (naproxen, 3.14 g, 13.6 mmol), 1,3-dihydroxy-acetone (3.11 g, 34.5 mmol) and N,N-dimethylaminopyridine (DMAP,1.4 g, 11.5 mmol) in acetone (100 mL) and stirred at ambient temperature overnight. The byproduct, dicyclohexyl urea was removed by filtration. The filtrate was concentrated and the residue was dissolved in CH2Cl2 (150 mL), washed with 3N HCl (150 mL), water (150 mL×3), brine, and dried over Na2SO4, filtered and concentrated. The product was separated by silica gel column chromatography eluting with ethyl acetate/hexane (1:2, Rf=0.13) to obtained a mixture of the title compound and its dimer. The reaction mixture was treated with ethyl ether and the dimer was removed by filtration. The filtrate was concentrated and dried under vacuum to give the title compound as a sticky oil (1.59 g). The resulted material was use in the next step without further purification. Mass spectrum (API-TIS) m/z 303 (MH)+.

Aufarbeitung

  1. customThe byproduct, dicyclohexyl urea was removed by filtration
  2. concentrationThe filtrate was concentrated
  3. dissolutionthe residue was dissolved in CH2Cl2 (150 mL)
  4. washwashed with 3N HCl (150 mL), water (150 mL×3), brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was separated by silica gel column chromatography
  9. washeluting with ethyl acetate/hexane (1:2, Rf=0.13)
  10. customto obtained

Quellen und Nachweise

ORD-Eintrag
ord-3c350739d8d44b448cbfa7d6ae6c83e5
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088762B2

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