反应详情

温度

55 °C

(2.6 g, 5.78 mmol) prepared in the previous step was combined with 26 mL of dioxane and 29 mL of 1N LiOH. The mixture was heated at 55° C. overnight. After the disappearance of 16D as monitored by LC/MS, the reaction was cooled to RT and approximately 50 mL of 1N HCl was added directly. The aqueous mixture was extracted with ethyl acetate (3×40 mL), washed with brine, dried over MgSO4, and concentrated in vacuo to afford 1-(1-(benzyloxycarbonyl)piperidin-3-yl)-2-oxo-5-phenyl-2,3-dihydro-1H-imidazole-4-carboxylic acid as an oil (16E) (2.43 g, quantitative yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.13 (d, J=9.60 Hz, 1H) 1.25 (br. s., 1H) 1.61-1.77 (m, 2H) 2.60 (br. s., 1H) 3.25 (br. s., 1H) 3.84-4.00 (m, 2H) 4.99 (s, 2H) 7.27-7.47 (m, 10H) 7.92-7.97 (m, 1H) 10.79 (s, 1H) 12.43 (br. s., 1H). This was used in next step without purification. ESI-MS: m/z 422.3 (M+H)+.

1. custom(2.6 g, 5.78 mmol) prepared in the previous step
2. temperaturethe reaction was cooled to RT
3. extractionThe aqueous mixture was extracted with ethyl acetate (3×40 mL)
4. washwashed with brine
5. dry with materialdried over MgSO4
6. concentrationconcentrated in vacuo