反応 #531859

反応方程式

8-bromooctanoic acid

ethanol

EDCI

→

8-bromooctanoic acid ethyl ester

収率 76.1%

溶媒

methylene chloride

反応条件

後処理

1. 1
   洗浄the reaction mixture was washed with 1 N NaOH aqueous solution (15 mL) and water (30 mL)
2. 2
   乾燥the organic layer was dried over Na2SO4
3. 3
   その他evaporated

実験手順

To a solution of 8-bromooctanoic acid (0.20 g, 0.89 mmol), DMAP (0.12 g, 0.99 mmol), and ethanol (0.05 g, 0.99 mmol) in methylene chloride (20 mL) was added EDCI (0.19 g, 0.99 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 evaporated to give 8-bromooctanoic acid ethyl ester (0.17 g, 75%). This bromide reacted with 4-(3-adamantan-1-yl-ureido)butyric acid 822 in the same manner as that used for the preparation of 883 to provide 879 (0.19 g, 65%) as a solid: 1H NMR (CDCl3) 1.26 (3H, t, J=6.9 Hz), 1.32-1.35 (6H, m), 1.59-1.66 (10H, m), 1.82 (2H, quint, J=6.9 Hz), 1.94-1.97 (6H, m), 2.05-2.07 (3H, m), 2.28 (2H, t, J=6.9 Hz), 2.36 (2H, t, J=6.9 Hz), 3.16 (2H, q, J=6.9 Hz), 4.05-4.14 (5H, m), 4.31 (1H, s); LC-MS (ESI) m/z calcd for C25H42N2O5 [M+H]+ 451.31. found [M+H]+ 451.20; mp 58-59 C. Anal. (C25H42N2O5) C, H, N.

出典