Sulfuric Acid → HCID 21197492, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of L-glutamic acid-5-benzylester (Fluka, 3.0 g, 0.013 mol) and sodium bromide (Fisher, 4.6 g, 0.044 mol) in aqueous hydrobromic acid (Fluka, 1 M, 22.5 mL) cooled to 0° C. was added portion wise sodium nitrite (Fluka, 1.6 g, 0.023 mol). After stirring for 2 h at 0° C., concentrated sulphuric acid (Merck, 1.2 mL) was added followed by diethyl ether (Eternell). The water phase was extracted three times with diethyl ether. The combined organic phases was washed four times with brine, dried over sodium sulphate and evaporated under reduced pressure. The crude product was purified using normal phase chromatography (Silica column (40 g), solvents: A=hexane, B=ethyl acetate, gradient: 10-35% B over 20 min, flow rate 40 mL/min, UV detection at 214 and 254 nm) affording 1.81 g of the pure product. Yield 46%. Structure verified by NMR.

Provenance & Evidence