Réaction #531862

Équation de réaction

4-(3-adamantan-1-yl-ureido)butyric acid

alcohol

4-hydroxymethylbenzoic acid ethyl ester

EDCI

→

849

Rendement 76.2%

4-[4-(3-Adamantan-1-yl-ureido)butyryloxymethyl]benzoic Acid Ethyl Ester

Rendement 76.2%

Solvants

methylene chloride

Conditions de réaction

Traitement

1. 1
   Lavagethe reaction mixture was washed with 1 N NaOH aqueous solution (15 mL) and water (30 mL)
2. 2
   Séchagethe organic layer was dried over Na2SO4
3. 3
   Concentrationconcentrated
4. 4
   AutreThen the residue was purified by column chromatography on silica gel
5. 5
   Lavageeluting hexane and ethyl acetate (5:1)

Mode opératoire

To a solution of 4-(3-adamantan-1-yl-ureido)butyric acid 822 (1.23 g, 0.83 mmol), DMAP (0.05 g, 0.42 mmol), and the above alcohol (0.15 g, 0.83 mmol) in methylene chloride (30 mL) was added EDCI (0.16 g, 0.83 mmol) at room temperature. After stirring for 12 h, the reaction mixture was washed with 1 N NaOH aqueous solution (15 mL) and water (30 mL), and the organic layer was dried over Na2SO4 and concentrated. Then the residue was purified by column chromatography on silica gel eluting hexane and ethyl acetate (5:1) to provide 849 (0.28 g, 75%) as a white solid: 1H NMR (CDCl3) 1.40 (3H, t, J=6.9 Hz), 1.66-1.68 (6H, m), 1.84 (2H, quint, J=6.9 Hz), 1.94-1.96 (6H, m), 2.05-2.07 (3H, m), 2.44 (2H, t, J=6.9 Hz), 3.17 (2H, q, J=6.9 Hz), 4.02 (1H, s), 4.17 (1H, s), 4.38 (2H, q, J=6.9 Hz), 5.17 (2H, s), 7.40 (2H, d, J=7.8 Hz), 8.00 (2H, d, J=7.8 Hz); LC-MS (ESI) m/z calcd for C25H34N2O5 [M+H]+ 443.25. found [M+H]+ 443.25; mp 96-99 C. Anal. (C25H34N2O5) C, H, N.

Source