Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 86606874, compound

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Reaction Steps

3-cyano-N-{(2S)-2-(3,4-dichlorophenyl)-4-[3-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)azetidin-1-yl]butyl}-N-methyl-1-naphthamide diacetate (see Example 25; 35 mg, 0.058 mmol) was dissolved in a few drops of acetone-water (1:1) and to the resultant solution was added pyridinium p-toluenesulfonate (43 mg, 0.17 mmol). The mixture was subjected to microwave single node heating for 10 min and then the solvent was removed by evaporation. The residue was dissolved in CH2Cl2 and the solution was washed with NaHCO3 aq. then dried over MgSO4. Removal of solvent by evaporation yielded an oil, which was purified by reversed phase chromatography using a mixture of acetonitrile and 0.1 M ammonium acetate aq. There was obtained 35 mg (89%) of the title compound as a white solid. 1H NMR (400 MHz, CD3OD): 1.4-2.2 (cm, 3H), 1.9 (s, 6H), 2.3-4.0 (cm, 20H), 6.4-7.8 (cm, 7H), 8.0-8.2 (cm, 1H), 8.6 (d, 1H); LCMS: m/z 563 (M+1)+.

Provenance & Evidence