Triethylamine → tert-Butyl (3-[cyclopropyl(pyridin-4-ylmethyl)amino]-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-3-oxopropyl)carbamate

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Reaction Steps

3-[tert-Butoxycarbonyl)amino]-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanoic acid from Example 9, Step 3 (1 eq.) was combined with 1-hydroxybenzotriazole hydrate (1.5 eq.) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide HCl salt (1.5 eq.) in chloroform (0.08 M). To this yellow solution was then added Amine 46 (4 eq.) and triethylamine (1.5 eq.). The resulting brown solution was stirred at RT for 48 h. The reaction solution was diluted with EtOAc and washed with H2O. The aqueous washes were back extracted with EtOAc. The combined organic extracts were washed with brine, dried over MgSO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 2:3 (v/v) Hex:EtOAc→EtOAc) afforded the title compound.

Provenance & Evidence