Acetic Acid → HCID 54579374, compound

Participants

Reaction Steps

A solution of 5-{5-[2-ethyl-3-(3-oxopropyl)phenyl]-1,3-thiazol-2-yl}-2-[(1-methyl ethyl)oxy]benzonitrile (D115) (150 mg, 0.371 mmol), 3-azetidinecarboxylic acid (75.0 mg, 0.742 mmol) and acetic acid (0.1 ml, 1.747 mmol) was stirred at room temperature for 15 min, then sodium triacetoxyborohydride (236 mg, 1.112 mmol) was added. The mixture was stirred at room temperature for 2 h. After concentration, the residue was partitioned between ethyl acetate and aqueous HCl (2M). The organic phase was concentrated and purified by Mass Directed AutoPrep to afford 1-{3-[3-(2-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,3-thiazol-5-yl)-2-ethyl phenyl]propyl}-3-azetidinecarboxylic acid (E93) (80 mg) as a TFA salt.

Provenance & Evidence