تفاعل #531863

معادلة التفاعل

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

4-hydroxyphenylacetic acid

EDCI

bromoethane

K2CO3

→

852

المردود 20.0%

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

المردود 20.0%

المذيبات

methylene chloride

DMF

ظروف التفاعل

المعالجة

1. 1
   غسيلthe reaction mixture was washed with water (20 mL)
2. 2
   workup.DISSOLUTIONthe methylene chloride solution dissolving the product
3. 3
   تجفيفwas dried over Na2SO4
4. 4
   تركيزconcentrated
5. 5
   أخرىto give
6. 6
   workup.STIRRINGstirred for 12 h at room temperature
7. 7
   استخلاصThe ethyl ester product was extracted with ether (30 mL)
8. 8
   غسيلthe ether solution was washed with 1 N NaOH aqueous solution (20 mL) and water (30 mL)
9. 9
   تجفيفdried over Na2SO4
10. 10
    تركيزconcentrated
11. 11
    أخرىThe residue was purified by column chromatography on silica gel
12. 12
    غسيلeluting hexane and ethyl acetate (5:1)

الإجراء التجريبي

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.

المصدر