p-Toluenesulfonic acid monohydrate → HCID 57920108, compound

Participants

Reaction Steps

In a round bottom flask under argon was placed 2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-5,5-dimethyl-hexanoic acid [1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl-methyl)-1H-pyrazol-3-yl]-amide (14 mg, 0.026 mmol) in methanol (2 mL). To this mixture was then added p-toluenesulfonic acid monohydrate (1 mg, 0.004 mmol) and stirred at 25° C. for 16 h. After this time period, the mixture was concentrated in vacuo and purified by AnaLogix IntelliFlash flash chromatography (4 g column, 100% ethyl acetate to 40% methanol/ethyl acetate) To afford 2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-5,5-dimethyl-hexanoic acid [1-((R)-2,3-dihydroxy-propyl)-1H-pyrazol-3-yl]amide (10 mg, 77%) as a white foam: HR-ES-MS m/z calculated for C24H31N4O5Cl [M+H]+ 491.2056, observed 491.2052; 1H NMR (300 MHz, CDCl3) δ ppm 0.91 (br. s., 9H), 1.04-1.35 (m, 2H), 1.79 (br. s., 1H), 1.99 (br. s., 1H), 3.38-3.84 (m, 2H), 3.97-4.29 (m, 4H), 4.41 (d, J=17.8 Hz, 1H), 4.66 (br. s., 1H), 4.86 (br. s., 1H), 6.65 (br. s., 1H), 7.26 (br. s., 4H), 7.47 (br. s., 1H), 9.56 (br. s., 1H).

Provenance & Evidence