2-Methyl-2-butene → HCID 89253167, compound

Participants

Reaction Steps

To a stirring solution of 4-((4-methoxy-N-(4-oxobutyl)benzamido)methyl)phenyl 4-(heptyloxy)benzoate INT-8 (264 mg, 0.484 mmol) in tert-butanol (12 mL) was added 2-methylbut-2-ene (4.7 ml, 44.4 mmol). A solution of sodium chlorite (400 mg, 4.42 mmol) and sodium dihydrogen phosphate (400 mg, 3.33 mmol) in H2O (2.5 mL) were added and the reaction stirred for 1 h at room temperature. The reaction was quenched with aq. Na2S2O5 (10 mL) and brine (10 mL). The aqueous phase was extracted with DCM and the combined organic phases were dried over MgSO4 and concentrated. The crude product was purified by chromatography (EA/hexanes) to provide 150 mg (55%) of 4-(N-(4-((4-(heptyloxy)benzoyl)oxy)benzyl)-4-methoxybenzamido)butanoic acid 88. LCMS-ESI (m/z) calculated for C33H39NO7: 561; found 560 [M−H]−, tR=9.53 min (Method 4).

Provenance & Evidence