N,N-Dimethylglycine → HCID 86609335, compound

Participants

Reaction Steps

[(5S)-3-(5-{2-fluoro-4[(5R)-2-oxo-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-3-yl]phenyl}pyridin-2-yl)-4,5-dihydroisoxazol-5-yl]methyl 5-(methylamino)pentanoate (Example 37: 134 mg, 0.23 mMol), N,N-dimethylglycine (140 mg, 1.36 mMol), 1,3-diisopropylcarbodiimide (121 mg, 0.96 mMol), and 4-dimethylaminopyridine (5 mg, 0.04 mMol) were suspended in 2 ml of DMF at room temperature. The mixture was stirred one day, diluted with ethyl acetate, washed with saturated aqueous sodium bicarbonate, dried over sodium sulfate and evaporated. The residue was purified by chromatography (silica gel; elution with 1 to 10% methanol in dichloromethane) to give the title compound as the free base. The sample was dissolved in methylene chloride (0.5 ml), treated with HCl (4M solution in dioxane, 0.05 ml) and diluted with diethyl ether (10 ml). The suspension was sonicated and triturated, the solution was decanted from the solids which were resuspended in diethyl ether followed by further sonication then filtration. The solid was dried in vacuo to yield the hydrochloride salt of the title compound as a light yellow solid (95 mg), melting point: 133° C.

Provenance & Evidence