3339-73-9, name is 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid
A mixture of phthalic anhydride and beta-alanine were heated to 190-200C in a sealed tube. Stirred for additional 30min at 190-200C after the solids totally melted. The reaction mixture was cooled to room temperature and 50% EtOH/water was added. The resulted suspension was filtered and the white precipitate was further washed with 50% EtOH/water, and then dried under vacuum overnight to give the N- phthaloyl-beta-alanine. Phosphoryl chloride was added to a suspension of N-phthaloyl- beta-alanine and phenylethylamine in acetionitrile. The suspension was stirred for 6h under reflux. Acetonitrile and phosphoryl chloride was removed by vacuum. The reaction mixture was then diluted with DCM and washed with sat NaHCC>3 solution, water and brine, then dried over anhydrous Na2S04. The filtrate was concentrated and the residue was purified by column chromatography using acetonitrile (0 to 20 %) in DCM as eluent to afford the imine compound. Acetic acid and sodium triacetoxyborohydride were added to a solution of imine compound in DCM and stirred for lh at room temperature. The reaction mixture was then washed with sat NaHCC>3 solution, water and brine, then dried over anhydrous Na2S04. The filtration was concentrated and the residue was purified by column chromatography using acetonitrile (0 to 50%) in DCM as eluent to give the amine compound. Cis-l ,2-Cyclohexanedicarboxylic anhydride was added to a solution of amine compound in p-xylene at 50C and stirred for 3h. The reaction mixture was concentrated under vacuum and the residue was purified by column chromatography using acetonitrile (0 to 20% with 1% AcOH) in DCM as eluent to give the designed product. Two diastereomers were separated by HPLC using water plus 0.1 %TFA and acetonitrile plus 0.1 %TFA as solvents.
The synthetic route of 3339-73-9 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; THE BROAD INSTITUTE, INC.; HU, Longqin; MAGESH, Sadagopan; CHEN, Lin; LEWIS, Timothy; MUNOZ, Ben; WANG, Lili; WO2013/67036; (2013); A1;,
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