HCID 23322744, compound → HCID 23322757, compound

Participants

Reaction Steps

Add 170 mg of this azide to a suspension of 30 mg NaH in 3 ml THF followed by a solution of 400 mg methyl 2-iodoproprionate in 2 ml THF. Heat the reaction mixture under nitrogen at 55° for 18 hr. Cool the reaction and add a few drops of H2O followed by ether. Wash the mixture with 5% NaHSO3, water, and brine. Dry the organic phase and concentrate in vacuo. Chromatograph this crude product on silica gel eluting with ethyl acetatehexane and isolate 3-azido-1-(1-carbomethoxyethyl)- perhydroazonin-2-one. Hydrolyze this ester in 1M NaOH. Acidify the reaction and extract with methylene chloride to obtain 3-azido-1-(1-carboxyethyl)perhydroazonin-2-one. Separate the diastereomers by reverse phase chromatography using acetonitrile-water mixtures.

Provenance & Evidence