Ammonia → HCID 18759733, compound

Participants

Reaction Steps

To a stirred solution of Part C acid (1.21 g, 7.02 mmol) in 50 mL of toluene was added 3 mL of oxalyl chloride. This reaction mixture was stirred for 1 hour at room temperature under argon and concentrated in vacuo. The residue was diluted with 20 mL of toluene and concentrated again. This was repeated to remove traces of oxalyl chloride. The residue was stirred at room temperature under argon in 5 mL of CH3OH and (C2H5)3N (1.17 mL, 8.43 mmol), and an excess of 9M methanolic ammonia (2 mL) was added. After stirring for 16 hours, the reaction mixture was partitioned between 3 mL water and 20 mL EtOAc. The aqueous layer was extracted twice more with EtOAc (20 mL). The combined organic layers were washed with NaCl, dried over MgSO4, filtered, and concentrated in vacuo to obtain a semi-solid. The semi-solid was crystallized by trituration with hexane to obtain 0.5 g (42%) of the desired title product as a solid.

Provenance & Evidence