反应详情

The title compound was prepared by a procedure described in J. Med. Chem. 2004, 47, 2110. To a suspension of 4-aminobutyric acid (2.79 g, 27.1 mmol) in DMF (40 mL) was added 1-adamantyl isocyanate (1.20 g, 6.77 mmol) at room temperature. The reaction mixture was stirred for 24 h. Then 1 N HCl aqueous solution (40 mL) was added into the reaction, and the mixture was stirred for 30 min. The solid crystalline product was filtered and washed with water (20 mL) and ethyl acetate (20 mL). The resulting solid was dried in a vacuum oven to give 1.90 g (100%) of 4-(3-adamantan-1-yl-ureido)butyric acid 822 as a white solid: 1H NMR (CD3OD): 1.66-1.75 (8H, m), 1.94-1.97 (6H, m), 2.05-2.07 (3H, m), 2.30 (2H, t, J=6.9 Hz), 3.08 (2H, q, J=6.9 Hz), 3.32 (2H, s); LC-MS (ESI) m/z calcd for C15H24N2O3 [M+H]+ 281.18, found [M+H]+ 281.25; mp 165 C. Anal. (C15H24N2O3) C, H, N.

1. stirringthe mixture was stirred for 30 min
2. filtrationThe solid crystalline product was filtered
3. washwashed with water (20 mL) and ethyl acetate (20 mL)
4. customThe resulting solid was dried in a vacuum oven