反応 #531863

反応方程式

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

4-hydroxyphenylacetic acid

EDCI

bromoethane

K2CO3

→

852

収率 20.0%

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

収率 20.0%

溶媒

methylene chloride

DMF

反応条件

後処理

1. 1
   洗浄the reaction mixture was washed with water (20 mL)
2. 2
   workup.DISSOLUTIONthe methylene chloride solution dissolving the product
3. 3
   乾燥was dried over Na2SO4
4. 4
   濃縮concentrated
5. 5
   その他to give
6. 6
   workup.STIRRINGstirred for 12 h at room temperature
7. 7
   抽出The ethyl ester product was extracted with ether (30 mL)
8. 8
   洗浄the ether solution was washed with 1 N NaOH aqueous solution (20 mL) and water (30 mL)
9. 9
   乾燥dried over Na2SO4
10. 10
    濃縮concentrated
11. 11
    その他The residue was purified by column chromatography on silica gel
12. 12
    洗浄eluting hexane and ethyl acetate (5:1)

実験手順

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.

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