Triethylamine → HCID 15231959, compound

Participants

Reaction Steps

To a solution of 1-adamantyl carboxylic acid (0.04 g, 0.21 mmol) in dry toluene (5 mL) is added phosphoryl azide (0.06 g, 0.21 mmol) and triethyl amine (0.02 g, 0.21 mmol). The resulting mixture is heated to reflux for 4 hours. [R--(R*,R*)] and [S--(R*,R*)]-N-(2-amino-1,2-diphenylethyl)-N'-[4-(trifluoromethyl)-phenyl]urea (0.1 g, 0.25 mmol) is then added and the mixture is allowed to cool to room temperature. The solution is concentrated in vacuo and the residue dissolved in CH2Cl2 and washed with aqueous 1N NaOH, saturated aqueous NaCl, and dried over MgSO4. Filtration and concentration provides an oil which is purified by flash chromatography (SiO2, EtOAc/hexane eluent). The solid product is triturated in diethyl ether and filtered to provide 0.06 g (48%) of a white solid, mp 236°-237° C. NMR (DMSO-d6): 1.47-1.92 (m, 15H), 4.89 (m, 2H), 5.74 (s, 1H), 6.35 (d, 1H, J=7.8 Hz), 6.90-7.21 (m, 11H), 7.56 (m, 4H), 9.13 (s, 1H). Analysis calculated for C33H35F3N4O2.0.2H2O: C, 68.20; H, 6.16; N, 9.64. Found: C, 68.22; H, 6.16; N, 9.53.

Provenance & Evidence