Réaction #531856

Équation de réaction

HCl

4-aminobutyric acid

DMF

1-adamantyl isocyanate

→

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

Rendement 100.0%

title compound

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

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGthe mixture was stirred for 30 min
2. 2
   FiltrationThe solid crystalline product was filtered
3. 3
   Lavagewashed with water (20 mL) and ethyl acetate (20 mL)
4. 4
   AutreThe resulting solid was dried in a vacuum oven

Mode opératoire

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.

Source