4-(Heptyloxy)benzoyl chloride → 4-(3-(Tert-butoxy)-2-(4-nitrobenzamido)-3-oxopropyl)-2-methoxyphenyl 4-(heptyloxy)benzoate

Participants

Reaction Steps

Prepared using General Procedure 3: To a stirred solution of tert-butyl 3-(4-hydroxy-3-methoxyphenyl)-2-(4-nitrobenzamido)propanoate INT-7 (1.34 g, 3.05 mmol) and TEA (1.28 mL, 9.15 mmol) in DCM (8 mL) at 0° C. was added 4-(heptyloxy)benzoyl chloride (0.81 mL, 3.36 mmol) dropwise. After warming to room temperature and stirring for 1 h, the mixture was quenched with saturated aqueous NaHCO3 (100 mL) and diluted with DCM (100 mL). The organic layer was dried over MgSO4 and concentrated. The product was purified by chromatography (EA/hexanes) to afford 1.70 g (86%) of 4-(3-(tert-butoxy)-2-(4-nitrobenzamido)-3-oxopropyl)-2-methoxyphenyl 4-(heptyloxy)benzoate INT-8. LCMS-ESI (m/z) calculated for C35H42N2O9: 634; no mass ion observed, tR=3.26 min (Method 4).

Provenance & Evidence