4-Methylmorpholine → HCID 54193900, compound

Participants

Reaction Steps

Combine (R)-2-bromo-3-phenylpropionic acid (3.44 g, 15 mmol), diethyl aminomalonate hydrochloride (4.23 g, 20 mmol), and N-methylmorpholine (5.5 mL, 50 mmol) in dichloromethane (50 mL). Add 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloric acid salt (3.83 g, 20 mmol) and 1-hydroxybenztriazole hydrate (2.70 g, 20 mmol). Add tetrahydrofuran (10 mL). After 20 hours, concentrate in vacuo and partition the concentrated reaction mixture between an aqueous 5% sulfuric acid solution and methyl t-butyl ether. Separate the layers and extract the organic layer with a saturated aqueous sodium bicarbonate solution and then brine. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with 1/4 ethyl acetate/hexane, 1/3 ethyl acetate/hexane, and then 2.5/1 ethyl acetate/hexane to give diethyl 2-((R)-2-bromo-3-phenylpropionylamino)malonate.

Provenance & Evidence