603-62-3Relevant articles and documents
Chemoenzymatic synthesis of apremilast: A study using ketoreductases and lipases
Vega, Kimberly B.,Cruz, Daniel M. V.,Oliveira, Artur R. T.,Da Silva, Marcos R.,De Lemos, Telma L. G.,Oliveira, Maria C. F.,Bernardo, Ricardo D. S.,De Sousa, Jackson R.,Zanatta, Geancarlo,Nasário, Fábio D.,Marsaioli, Anita J.,De Mattos, Marcos C.
, p. 1100 - 1110 (2021/05/19)
The key step in the chemoenzymatic synthesis of apremilast was to produce the chiral alcohol (R)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethanol, (R)-3. Two enzymatic approaches were evaluated to obtain (R)-3, one using ketoreductases and the other lipases. Bioreduction of 1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethanone (2), using ketoreductase KRED.P2-D12, led to (R)-3 with 48% conversion and 93% enantiomeric excess (ee). Kinetic resolution of rac-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl acetate (rac-4), via hydrolysis reaction, with 20% of n-butanol, catalyzed by lipase from Aspergillus niger yielded (R)-3 with > 99% ee, 50% conversion and E-value (enantiomeric ratio) > 200. The reaction between enantiomerically pure (R)-3 and 4-acetylamino-isoindol-1,3-dione (8) afforded apremilast in 65% yield and 67% ee.
Grinding imidation of anhydrides on smectite clays as recyclable and heterogeneous catalysts under solvent-free conditions
Marvi, Omid
, p. 3501 - 3504 (2017/08/14)
Imidation of various anhydrides employing solvent-free grindstone technique using smectite clays as recyclable and green catalysts was examined and obtained excellent yields.
An expedient and convenient approach for one-pot synthesis of 1H-isoindole-1,3(2H)-diones
Ekhtiari, Zeinab,Havasi, Forugh,Nikpour, Farzad
, p. 941 - 944 (2016/10/13)
An easy and expedient method for the one-pot synthesis of 1H-isoindole-1,3(2H)-diones has been developed by the reaction of the corresponding cyclic anhydrides with guanidinium chloride as a nitrogen source in the presence of FeCl3 as a catalyst under mild reaction conditions.
