Sodium Iodide → HCID 131714420, compound

Participants

Reaction Steps

A mixture of 428 mg (1 mmol) of L-leucyl-L-valyl-L-phenylalanine, methyl ester, hydrochloride, 150 mg (1 mmol) of sodium iodide and 19 mg (0.1 mmol) of sodium bisulfite (on the basis of this experiment, its use was abandoned in the preparation of other compounds) was treated with 1 ml of dry dimethylformamide under argon at room temperature. Solid sodium bicarbonate (176 mg, 2.1 mmol) was added followed by a solution of 298 mg (1 mmol) of [(phenylmethoxy)carbonyl]-L-leucine chloromethyl ketone in 1 ml of dimethylformamide. After stirring for 24 hours at room temperature, the reaction was diluted with 50 ml of ethyl acetate and rinsed with two 10 ml portions of water, 10 ml of dilute aqueous sodium bisulfite, two 10 ml portions of water and brine, dried (magnesium sulfate) and concentrated in vacuo to 580 mg of crude product. Flash chromatography on 40 g of LPS-1 silica gel using 5:1, petroleum ether:acetone yielded 263 mg of the title compound as an oil.

Provenance & Evidence