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

HRID 1362799

反応式

HRID 1362799 の反応式
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

参加物

5

反応物 3

HCID 670DihydroxyacetoneHCID 10868DicyclohexylcarbodiimideHCID 156391Naproxen

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒2 回

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-7eb7d8fd59614621952a49dbc6610309
出典データセット
uspto-grants-2011_02
特許番号
US07883714B2

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