110256-15-0, 5-Cyclopropylisoxazole-3-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated
Into a 500-mL round-bottom flask was placed 5-cyclopropyl-1,2-oxazole-3- carboxylic acid (6.12 g, 39.96 mmol, 1.00 equiv), tert-butyl (2R)-4-amino-2- methylpiperidine-1-carboxylate (8.57 g, 39.99 mmol, 1.00 equiv), dichloromethane (300 g), TEA (12.12 g, 120.00 mmol, 3.00 equiv) and HATU (22.8 g, 60.00 mmol, 1.50 equiv). The resulting solution was stirred for 15 h at room temperature. The resulting mixture was then washed with 2x100mL of Na2CO3 (1M, aq.). Then the organic phase was dried over Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography (C18 gel, CH3CN/H2O = 1:1) to give 10.8 g diastereomeric tert- butyl 4-(5-cyclopropylisoxazole-3-carboxamido)-2-methylpiperidine-1-carboxylate. Then the purified product was separated by Prep-SFC with the following conditions (prep SFC 350): Column, CHIRALPAK AD-H SFC, 5x25cm,5um; mobile phase, CO2(50%), methanol(50%); Detector, uv 220nm. This was resulted in 7.48 g (54%) of tert-butyl (2R,4R)-4-(5-cyclopropyl-1,2-oxazole-3-amido)-2-methylpiperidine-1-carboxylate as light yellow oil. 1H-NMR (300 MHz, CDCl3): 6.86 (d, J = 6.9 Hz, 1H), 6.33 (s, 1H), 4.30-4.15 (m, 2H), 3.93-3.80(m, 1H), 3.22-3.07(m, 1H), 2.20-1.90 (m, 3H), 1.79-1.65(m, 2H), 1.46(s, 9H), 1.26(d, J = 6.9 Hz, 3H), 1.17-1.06(m, 2H), 1.06-0.94(m, 2H) ppm. LCMS (method A, ESI): RT=1.46 min, m/z =372.2 [M+H]+. And 2.52 g (18%) of tert- butyl (2R,4S)-4-(5-cyclopropyl-1,2-oxazole-3-amido)-2-methylpiperidine-1-carboxylate as a light yellow solid. 1H-NMR (300 MHz, CDCl3): 6.55 (d, J = 8.1 Hz, 1H), 6.33 (s, 1H), 4.63-4.39 (m, 1H), 4.39-4.15(m, 1H), 4.15-3.95(m, 1H), 3.0-2.85 (m, 1H), 2.15- 1.98(m, 2H), 1.92-1.78(m, 1H), 1.65-1.50 (m, 1H), 1.46(s, 9H), 1.42-1.26 (m, 1H), 1.23(d, J = 6.9 Hz, 3H), 1.17-1.06(m, 2H), 1.06-0.94(m, 2H) ppm. LCMS (method A, ESI): RT=1.46 min, m/z =372.2 [M+H]+.
110256-15-0, The synthetic route of 110256-15-0 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; EPIZYME, INC.; MITCHELL, Lorna Helen; BELL, Andrew Simon; CHESWORTH, Richard; FOLEY, Megan Alene Cloonan; KUNTZ, Kevin Wayne; MILLS, James Edward John; MUNCHHOF, Michael John; (375 pag.)WO2016/40515; (2016); A1;,
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