Benzyltrimethylammonium methoxide → HCID 23388385, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 335 mg (1.68 mmol) 2-(cyclohexylamino)-3-methylbutyric acid (Example 69, Step A), 500 mg (1.68 mmol) 4,4-bis-(4-fluoro-phenyl)-butylamine monohydrochloride, 0.29 mL (1.68 mmol) N,N-diisopropylethylamine, and 1.5 mL (3.36 mmol) benzyltrimethylammonium methoxide (40% solution in methanol) in 4 mL dry DMF was cooled to 3° C., and 637° mg (1.68 mmol) O-benzotriazol-1-yl-N,N,N′,N′-bis(tetramethylene)uronium hexafluorophosphate was added and the resulting mixture stirred at 3° for 30 minutes, warmed to 25° C., and stirred an additional 30 minutes at which time it was diluted with 20 mL diethyl ether, and washed with 20 mL saturated aqueous sodiumbicarbonate solution and twice with 20 mL brine, dried over anhydrous sodium sulfate and concentrated at reduced pressure. The residue thus obtained was further purified by silica gel chromatography using 4:1 ethyl acetate:hexanes as eluant, followed by conversion to the hydrochloride salt by treating with excess diethyl ether which had been saturated with hydrogen chloride gas to give 29 mg (4%) of titled compound: mp 49-53° C. APCI-MS m/z 443.4 (MH+).

Provenance & Evidence