Reaktion #531863

Reaktionsgleichung

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

4-hydroxyphenylacetic acid

EDCI

bromoethane

K2CO3

→

852

Ausbeute 20.0%

4-(3-Adamantan-1-yl-ureido)butyric Acid 4-Ethoxycarbonylmethylphenyl Ester

Ausbeute 20.0%

Lösungsmittel

methylene chloride

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenthe reaction mixture was washed with water (20 mL)
2. 2
   workup.DISSOLUTIONthe methylene chloride solution dissolving the product
3. 3
   Trocknenwas dried over Na2SO4
4. 4
   Einengenconcentrated
5. 5
   Sonstigeto give
6. 6
   workup.STIRRINGstirred for 12 h at room temperature
7. 7
   ExtraktionThe ethyl ester product was extracted with ether (30 mL)
8. 8
   Waschenthe ether solution was washed with 1 N NaOH aqueous solution (20 mL) and water (30 mL)
9. 9
   Trocknendried over Na2SO4
10. 10
    Einengenconcentrated
11. 11
    SonstigeThe residue was purified by column chromatography on silica gel
12. 12
    Wascheneluting hexane and ethyl acetate (5:1)

Vorschrift

To a solution of 4-(3-adamantan-1-yl-ureido)butyric acid 822 (0.15 g, 0.54 mmol), DMAP (0.07 g, 0.54 mmol), and 4-hydroxyphenylacetic acid (0.09 g, 0.59 mmol) in methylene chloride (20 mL) was added EDCI (0.11 g, 0.59 mmol) at room temperature. After stirring for 12 h, the reaction mixture was washed with water (20 mL), and the methylene chloride solution dissolving the product was dried over Na2SO4 and concentrated to give conjugated product. This crude mixture in DMF (30 mL) was treated with bromoethane (0.15 g, 1.34 mmol) and K2CO3 (0.18 g, 1.34 mmol) at room temperature and stirred for 12 h at room temperature. The ethyl ester product was extracted with ether (30 mL), and the ether solution was washed with 1 N NaOH aqueous solution (20 mL) and water (30 mL), dried over Na2SO4, and concentrated. The residue was purified by column chromatography on silica gel eluting hexane and ethyl acetate (5:1) to give 852 (47 mg, 20%) as a white solid: 1H NMR (CDCl3) 1.40 (3H, t, J=6.9 Hz), 1.66-1.68 (6H, m), 1.89-1.95 (8H, m), 2.05-2.07 (3H, m), 2.62 (2H, t, J=6.9 Hz), 3.25 (2H, q, J=6.9 Hz), 3.60 (2H, s), 4.07 (1H, s), 4.16 (2H, q, J=6.9 Hz), 4.29 (1H, s), 7.08-7.10 (2H, m), 7.28-7.30 (2H, m); LC-MS (ESI) m/z calcd for C25H34N2O5 [M+H]+ 443.25. found [M+H]+ 443.25; mp 95-97 C. Anal. (C25H34N2O5) C, H, N.

Quelle