Reaktion #531862

Reaktionsgleichung

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

alcohol

4-hydroxymethylbenzoic acid ethyl ester

EDCI

→

849

Ausbeute 76.2%

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

Ausbeute 76.2%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle