Dicyclohexylcarbodiimide → Tert-butyl 3-(3-((2-morpholinoethoxy)carbonyl)benzyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate

Participants

Reaction Steps

To a solution of 3-((8-(tert-butoxycarbonyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoic acid (0.3 g, 0.65 mmol), dicyclohexylcarbodiimide (0.16 g, 0.78 mmol) and 4-(dimethylamino)pyridine (0.01 g, 0.078 mmol) in dichloromethane (10 mL), was added hydroxyethyl morpholine (0.037 g, 0.32 mmol, d=1.072). After stirring at room temperature for 18 hours, the reaction mixture was filtered, concentrated in vacuo and isolated by preparatory TLC (5% methanol/dichloromethane) to obtain the title compound (0.22 g, 59%); 1H NMR (DMSO-d6): δ 1.45 (s, 9H), 1.59-1.66 (m, 4H), 2.43-2.48 (m, 4H), 2.66 (t, 2H, J=5.6 Hz), 3.32-3.51 (m, 4H), 3.89 (br, 2H), 3.90 (br, 2H), 4.37 (t, 2H, J=5.6 Hz), 4.62-4.65 (m, 4H), 6.68 (d, 2H, J=8.4 Hz), 6.77 (t, 1H, J=7.2 Hz), 7.17 (t, 2H, J=8.8 Hz), 7.53-7.61 (m, 2H), 7.86-7.90 (m, 2H); MS for C32H42N4O6 m/z 579.09(M+H)+.

Provenance & Evidence