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
Step 2: Synthesis of (2S)-tert-butyl 4-(5-cyclopropylisoxazole-3-carboxamido)-2- methylpiperidine-1-carboxylate [0269] Into a 1L round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed dichloromethane (500 mL), HOBT (15 g, 111.01 mmol, 1.53 equiv), EDCI (20 g, 104.33 mmol, 1.44 equiv), 5-cyclopropyl-1,2-oxazole-3-carboxylic acid (13.3 g, 86.85 mmol, 1.20 equiv) and tert-butyl (2S)-4-amino-2-methylpiperidine-1- carboxylate (15.5 g, 72.33 mmol, 1.00 equiv).Then triethylamine (36 g, 355.77 mmol, 4.92 equiv) was added dropwise. The resulting solution was stirred for 2 hours at 25oC. The resulting mixture was concentrated under vacuum. The resulting solution was diluted with 500 mL of ethyl acetate. The resulting mixture was washed with 3×500 mL of water. The residue was purified on a silica gel column with ethyl acetate/petroleum ether (1:10). This resulted in 14 g (55%) of tert-butyl (2S)-4-(5-cyclopropyl-1,2-oxazole-3-amido)-2- methylpiperidine-1-carboxylate as light yellow oil. LCMS (method A, ESI): RT=2.05 min, m/z =350.2 [M+H]+. Step 3: Synthesis of tert-butyl (2S,4S)-4-(5-cyclopropyl-1,2-oxazole-3-amido)-2- methylpiperidine-1-carboxylate and tert-butyl (2S,4R)-4-(5-cyclopropyl-1,2-oxazole-3- amido)-2-methylpiperidine-1-carboxylate [0270] The crude product was purified by Chrial-HPLC with the following conditions: Column name: CHIRALPAK AD-H, 4.6*150mm,5um,Co-Solvent: EtOH(0.1%DEA), %Co-Solvent: Hexane,25.000, Detector: 220nm. The resulting solution was concentrated under vacuum. This resulted in 9.8 g (70%) of tert-butyl (2S,4S)-4-(5-cyclopropyl-1,2- oxazole-3-amido)-2-methylpiperidine-1-carboxylate as white solid. 1H-NMR (400 MHz, DMSO): 8.54-8.52 (m, 1H), 6.47 (s, 1H), 3.94-3.87(m, 2H), 3.57-3.53(m, 1H), 3.32- 3.26(m, 1H), 2.20-2.16(m, 1H), 1.80-1.63(m, 4H), 1.39(s, 9H), 1.16-1.15(m, 3H), 1.10- 1.06(m, 2H), 0.93-0.89(m, 2H) ppm. And 3.3 g (24%) of tert-butyl (2S,4R)-4-(5- cyclopropyl-1,2-oxazole-3-amido)-2-methylpiperidine-1-carboxylate as a light yellow solid. 1H-NMR (400 MHz, DMSO): 8.54-8.52 (m, 1H), 6.46 (s, 1H), 4.54-4.30(m, 1H), 4.28-4.04(m, 1H), 4.00-3.68(m, 1H), 3.10-2.70(m, 1H), 2.19-2.15(m, 1H), 1.76-1.73(m, 1H), 1.63-1.59(m, 2H), 1.39-1.35(m, 10H), 1.13-1.08(m, 5H),1.00-0.82(m, 2H) ppm.
110256-15-0, 110256-15-0 5-Cyclopropylisoxazole-3-carboxylic acid 1092113, aIsoxazoles compound, is more and more widely used in various fields.
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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