p-Toluenesulfonic acid → 1-(2,2-Dimethylpropyl)-5-[(1E)-4-hydroxybut-1-en-1-yl]-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

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Reaction Conditions

Reaction Steps

5-[(1E)-4-{[tert-Butyl(dimethyl)silyl]oxy}but-1-en-1-yl]-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (32-2, 207 mg, 0.51 mmol, 1.0 equiv) was added to anhydrous methanol (5.1 mL) and cooled to 0° C. p-Toluenesulfonic acid (9.7 mg, 0.05 mmol, 0.1 equiv) was added and the resulting solution was stirred at 0° C. for 18 h. Following this duration, LCMS showed complete consumption of 32-2. The contents were diluted ethyl acetate (15 mL) and saturated NaHCO3 (15 mL) and the layers were separated. The aqueous layer was back-extracted with ethyl acetate (3×15 mL) and the combined organics were dried over Na2SO4, filtered and concentrated in vacuo to give a pale yellow oil. Purification by reverse-phase HPLC (10-100% 0.1% TFA in H2O:CH3CN) afforded 32-3 as a colorless oil. MS m/z (M+H): calculated=290.1863; observed=290.1864.

Provenance & Evidence