Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 86670376, compound

Participants

Reaction Steps

A solution of ((2S)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)acetic acid hydrochloride (1.55 g, 3.01 mmol), N,O-dimethylhydroxylamine hydrochloride (0.323 g, 3.31 mmol, Sigma-Aldrich, St. Louis, Mo.), and Hünig's base (1.05 mL, 6.02 mmol) in DMF (20 mL) was stirred at 0° C. To this mixture was added HATU (1.26 g, 3.31 mmol). The reaction was stirred for 3 h at room temperature and then diluted with EtOAc (30 mL) and water (20 mL). The organic layer was separated and then washed with water (2×20 mL) and brine (20 mL). The combined organic extracts were dried over MgSO4, filtered, and concentrated. The crude material was absorbed onto silica gel and purified via column chromatography (80 g silica gel, 0 to 100% EtOAc in hexanes) to give N-methoxy-N-methyl-2-((2S)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)acetamide (1.48 g) as an orange oil.

Provenance & Evidence