反応 #502114

反応方程式

1,3-dicyclohexylcarbodiimide

(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

1,3-dihydroxy-acetone

→

title compound

3-Hydroxy-2-oxopropyl(2S)-2-(6-methoxy(2-naphthyl))propanoate

溶媒

acetone

acetone

反応条件

後処理

1. 1
   その他The byproduct, dicyclohexyl urea was removed by filtration
2. 2
   濃縮The filtrate was concentrated
3. 3
   workup.DISSOLUTIONthe residue was dissolved in CH2Cl2 (150 mL)
4. 4
   洗浄washed with 3N HCl (150 mL), water (150 mL×3), brine
5. 5
   乾燥dried over Na2SO4
6. 6
   ろ過filtered
7. 7
   濃縮concentrated
8. 8
   その他The product was separated by silica gel column chromatography
9. 9
   洗浄eluting with ethyl acetate/hexane (1:2, Rf=0.13)
10. 10
    その他to obtained

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)+.

出典