ORGANIC SPECTROSCOPY INTERNATIONAL: 2-(2-(4-(3-(4-Cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo- 2-thioxoimidazolidin-l-yl)butanamido)ethoxy)ethyl 2-(adamantan-l-yl)acetate

Example 5; 2-(2-(4-(3-(4-Cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo- 2-thioxoimidazolidin-l-yl)butanamido)ethoxy)ethyl 2-(adamantan-l-yl)acetate

To a 1 dram vial with stirbar was charged 4-(3-(4-cyano-3-
(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-l-yl)butanoic acid (10.0 mg, 0.025 mmol), EDC (7.0 mg, 0.038 mmol), HOBt (6.0 mg, 0.375 mmol), and 0.35 mL dichloromethane. After 15 minutes of stirring 2-(2-aminoethoxy)ethyl 2-(adamantan-l-yl)acetate (8.0 mg, 0.027 mmol) was added and the mixture left stir for 16 h upon which the mixture was diluted with 1 mL dichloromethane and washed with 10% aq. citric acid (2 X 1 mL), and saturated a₂C03 (2 X 1 mL). The organic layer was dried with Na₂S0₄ and concentrated down to yield a crude oil which was purified by silica gel chromatography (dichloromethane to 19: 1 dichloromethane: MeOH) to yield 5 mg (30% yield) of pure product as an amber oil.

H NMR (500 MHz, CDC1₃) δ 7.93 (d, J= 8.3, 1H), 7.87 (d, J= 1.7, 1H), 7.75 (dd, J= 1.9, 8.3, 1H), 6.04 (t, J= 5.1, 1H), 4.25 - 4.14 (m, 2H), 3.79 - 3.71 (m, 2H), 3.68 - 3.61 (m, 2H), 3.55 (t, J = 5.0, 2H), 3.49 - 3.40 (m, 2H), 2.32 (t, J = 6.7, 2H), 2.14 (dt, J = 6.8, 14.4, 2H), 2.08 (s, 2H), 1.95 (s, 4H), 1.70-1.66 (m, 4H), 1.65-1.55 (m, 13 H);

¹³C NMR (126 MHz, CDCI₃) δ 178.6, 175.5, 172.0, 171.8, 137.3, 135.3, 133.6 (q, J = 33.4), 132.3, 127.2 (q, J= 4.7), 121.0 (q, J = 274.0), 115.0, 110.1 (q, J= 2.2), 69.7 69.3, 65.4, 62.7, 49.0, 43.7, 42.5, 39.4, 36.8, 33.0, 33.0, 28.7, 23.7, 23.2;

LRMS (ESI) 662.4 (M+H)⁺.

http://www.google.com/patents/WO2013170147A1?cl=en