HOAt → (R)-{2-methyl-2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-propionyl}-pyrrolidine-2-carboxylic acid ethyl ester

Participants

Reaction Steps

To a stirred solution of (R)-pyrrolidine-2-carboxylic acid ethyl ester hydrochloride (1.7 g, 9.4 mmot), TEA (1.0 g, 10.3 mmol) and the title C compound, 2-methyl-2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-propionic acid (3.0 g, 8.55 mmol) in DCM (50 mL) is added EDCl (2.0 g, 10.3 mmol) and 1-hydroxy-7-azabenzotriazole (HOAt, 1.2 g, 8.55 mmol) at RT. The reaction mixture is stirred for 48 h. The reaction mixture is diluted with ethyl acetate, washed with 2 N aqueous HCl, water, 2 N aqueous sodium hydroxide, water and brine, dried over anhydrous magnesium sulfate and concentrated at reduced pressure. The crude product is purified on a Biotage 40M column using 35% ethyl acetate in hexane to yield (R)-1-{2-methyl-2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-propionyl}-pyrrolidine-2-carboxylic acid ethyl ester as a clear oil.

Provenance & Evidence