* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With lithium hydroxide monohydrate In water at 8 - 12℃; for 16 h;
Example 14-[5-(3,5-Di-tert-butylphenyl)-l-[4-(4-methylpiperazine-l-carbonyl)phenyl]pyrazol-3- yl]benzoic acidCharge a reactor with THF (1790 L), methyl 4-[5-(3,5-di-tert-butylphenyl)-l-[4-(4-methylpiperazine-l-carbonyl)phenyl]pyrazol-3-yl]benzoate (358 g, 0.605 mol) and water (1 140 mL) at 8 - 12 °C. Add lithium hydroxide monohydrate (38 g, 0.905 mol) in one portion. Stir the mixture for 16 h at 8 - 12 °C. Add EtOAc (30 L) and adjust the mixture to pH = 5 with 1 N HC1. Separate the two phases and extract the aqueous layer with EtOAc (2 x 10 L). Combine the organic layers, dry with sodium sulfate, filter, and remove the solvent to give a solid. Purify the material by column chromatography, eluting with DCM/MeOH (20/1) to give the product as a pale yellow solid. Triturate the solid in a solvent mixture of acetonitrile/MTBE (1/3, 4 L) for 1 h. Filter to collect the solid and dry under vacuum at 50 °C for 72 h to give the title compound (264.2 g, 75percent) as a white solid. LC-ES/MS m/z 579 [M+H]+.
Reference:
[1] Patent: WO2013/66640, 2013, A1, . Location in patent: Page/Page column 39
[2] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 14, p. 3274 - 3277