Dihydroxyacetone → 3-Hydroxy-2-oxopropyl(2s)-2-(6-methoxy(2-naphthyl))propanoate

HRID 1873620

반응식

HRID 1873620 반응식
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

참가 물질

5

반응물 3

HCID 670DihydroxyacetoneHCID 10868DicyclohexylcarbodiimideHCID 156391Naproxen

생성물 1

HCID 210759643-Hydroxy-2-oxopropyl(2s)-2-(6-methoxy(2-naphthyl))propanoate

시약·촉매·용매 1

HCID 180Acetone용매2회

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-356d558596194fa3af70696c9c9db0b3
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304409B2

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