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.
Chemical synthesis method of lenalidomide key intermediate
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Paragraph 0021; 0022, (2020/08/26)
The invention relates to a chemical synthesis method of a lenalidomide key intermediate, i.e., 3-(4-nitro-1-oxo-1,3-dihydro-2H-isoindole-2-yl)piperidine-2,6-dione. The target compound 3-(4-nitro-1-oxo-1,3-dihydro-2H-isoindole-2-yl)piperidine-2,6-dione is prepared by taking a compound 3-nitrophthalic acid as a raw material through cyclization ammoniation, carbonyl reduction, condensation and selective oxidation. The synthesis method has the advantages of few reaction steps, easily available raw materials, mild reaction conditions, low equipment requirements, simple product separation and purification, environmental friendliness, simple operation, good safety, realization of another selection of a lenalidomide synthesis scheme, and good industrial application prospect.
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.
Luminol or isoluminol synthesizing method by one-pot process
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Paragraph 0060, (2017/08/30)
The invention discloses a luminol or isoluminol synthesizing method by a one-pot process. The luminol or the isoluminol synthesizing method by the one-pot process includes the steps of 1) enabling 3-nitrophthalic acid or 4-nitrophthalic acid as a starting material to react with urea in an organic solvent to obtain 3-nitrophthalimide or 4-nitrophthalimide; 2) enabling the 3-nitrophthalimide or the 4-nitrophthalimide to react with a hydrazine hydrate aqueous solution to obtain 3-nitrophthalhydrazide or 4-nitrophthalhydrazide; 3) enabling the 3-nitrophthalhydrazide or the 4-nitrophthalhydrazide to react with a reducing agent in the presence of a catalyst to obtain luminol or isoluminol. The luminol or the isoluminol synthesizing method by the one-pot process has the advantages of simplicity, convenience in operation, low cost, high yield and less pollution, and can be applicable to industrialized production.
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.
Transition metal-free 1,3-dimethylimidazolium hydrogen carbonate catalyzed hydration of organonitriles to amides
Verma, Praveen Kumar,Sharma, Upendra,Bala, Manju,Kumar, Neeraj,Singh, Bikram
, p. 895 - 899 (2013/04/23)
An efficient hydration of organonitriles to the corresponding amides was accomplished using 1,3-dimethylimidazolium hydrogen carbonate as an organocatalyst. The developed catalytic method was also applicable for the synthesis of metal phthalocyanines.
Substituent-guided switch between C-H activation and decarboxylative cross-coupling during palladium/copper-catalyzed cascade reactions of 2-aminobenzoates with 2-haloarylaldehydes
Bhowmik, Subhendu,Pandey, Garima,Batra, Sanjay
supporting information, p. 10487 - 10491 (2013/08/23)
Cascade switch: Phenanthridines, pyrazole[4,3-c]quinolines and isocryptolepine were prepared in one step from the Pd/Cu-catalyzed reaction between potassium 2-aminobenzoates and 2-haloarylaldehydes (see scheme). Although the reactions of 2-aminobenzoates proceeded via a cascade imination/C-H functionalization, the reactions of 6-nitro-2-aminobenzoates ensued via a tandem imination/decarboxylative cross-coupling. Copyright
Hydrazine-hydroquinone complex as an efficient solid phase hydrazine donor: High yield synthesis of luminol and isoluminol
Chattopadhyay, Gautam,Ray, Partha Sinha
experimental part, p. 326 - 328 (2011/10/02)
Isomeric aminophthalhydrazides, luminol and isoluminol were easily obtained from the corresponding aminoph-thalimides by solid phase hydrazinolysis with the hydrazine-hydroquinone complex in high yields. Synthesis of a novel chemiluminescent agent, a heterocyclic analogue of isoluminol related to aminoimidazolecarboxamide, is also described.
Synthesis of some nitrogen mustards (Mannich bases)
Sinha, Girish Kumar,Mehra,Kumar, Sharad
experimental part, p. 1261 - 1264 (2012/04/04)
Several Mannich base half nitrogen mustards have been synthesised by the condensation of 3-substituted phthalimides and 4-substituted phthalimides with (2-chloroethyl) amine in ethanol- formalin.
Unexpected reduction of N-hydroxyphthalimides to phthalimides-orthogonal reduction of functionalized N-hydroxyphthalimides
Jacq, Jér?me,Berthiol, Florian,Einhorn, Cathy,Einhorn, Jacques
body text, p. 2263 - 2266 (2010/11/24)
A chemoselective reduction of N-hydroxyphthalimides to phthalimides under mild conditions has been discovered. It involves reaction of an N-hydroxyimide with bis(pinacolato)diboron in the presence of a base. Other easily reducible functional groups, such as iodo, nitro, or azido groups are unaffected. Alternatively, such functional groups may be selectively reduced without affecting the N-hydroxyimide moiety using a set of classical conditions. Georg Thieme Verlag Stuttgart - New York.
