Toluene → HCID 131717576, compound

Participants

Reaction Steps

A solution of ethyl N-[2-(phosphonomethylamino)-3-(4-biphenylyl)-propionyl]-3-aminopropionate (0.3 g, 0.69 mmol), 18 crown-6 (0.36 g, 1.38 mmol) in toluene (12 mL) is cooled to 0° and is treated with potassium bis-trimethylsilylamide (2.22 mL, 1.45 mmol). After 7 minutes the clear solution is treated with iodomethyl pivalate (0.25 mL, 1.56 mmol) and stirred for 18 hours. Ethyl acetate is added, the mixture is washed with water, dried (Na2SO4), concentrated and the residue is chromatographed on silica gel (EtOAc/hexanes, 75:25) to obtain ethyl N-{2-[di-(pivaloyloxymethyl)-phosphonomethylamino]-3-(4-biphenylyl)propionyl}-3-aminopropionate as an oil.

Provenance & Evidence