Dimethylformamide → methyl ((S)-1-((S)-2-(5-bromo-1H-imidazol-2-yl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-yl)carbamate

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Reaction Steps

A mixture of Example 126F (3.99 g, 15.8 mmol), Example 126A (2.77 g, 15.8 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (3.63 g, 19.0 mmol), 1-Hydroxy-benzotriazole hydrate (2.90 g, 19.0 mmol) and N-methylmorpholine (12.2 mL, 111.0 mmol) in DMF (150 mL) were allowed to stir overnight. Mixture was diluted with H2O and extracted with EtOAc (3×300 mL). The organic was washed with H2O and Brine. The organic was then dried (MgSO4), filtered and concentrated. Purification by chromatography (silica gel, 75% EtOAc in Hexanes) afforded 5.2 g (88%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.79 (dd, J=6.67, 3.63 Hz, 6H), 1.84-1.96 (m, 3H), 2.02-2.14 (m, 2H), 3.51 (s, 3H), 3.66-3.80 (m, 2H), 3.96-4.03 (m, 1H), 4.91-4.99 (m, 1H), 7.06 (d, J=1.52 Hz, 1H), 7.26 (d, J=8.46 Hz, 1H), 12.01 (s, 1H). MS (ESI) m/z 373 (M+H)+.

Provenance & Evidence