3972-36-9Relevant articles and documents
Asymmetric hydrogenation of itaconic acids with rhodium(I)-phenyl-CAPP complex; a correction
Jendralla
, p. 3671 - 3672 (1991)
Asymmetric hydrogenation of itaconic acids 2 under homogeneous catalysis of neutral Rh-complex 3 gives substituted succinic acids 4 of (S)-configuration with > 95% ee.
A kind of improved mitiglinide industrial preparation method
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Paragraph 0035; 0038, (2017/08/25)
The invention provides an improved mitiglinide calcium (I) preparation method, and is characterized in that the preparation method successively comprises the steps: step 1, preparation of 2-benzyl succinic acid; step 2, preparation of (S)-2-benzyl succinic acid; step 3, preparation of 2-(S)-benzyl-4-oxo-(cis-perhydroisoindole-2-yl)butyric acid; and step 4, preparation of mitiglinide calcium. The invention provides the mitiglinide calcium industrialized preparation method having the advantages of being economical and practical, simple to operate, short in reaction period and high in yield.
Preparation method of (S)-2-benzylsuccinic acid
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Paragraph 0024; 0025; 0026; 0027, (2016/12/01)
The invention provides a preparation method of (S)-2-benzylsuccinic acid, and relates to a method for preparing (S)-2-benzylsuccinic acid from (R)-2-benzylsuccinic acid. After EDTA is added in an alkaline aqueous solution containing the (R)-2-benzylsuccinic acid, racemization can be implemented effectively. By the method provided by the invention, the (S)-2-benzylsuccinic acid can be prepared from a solution of 2-benzylsuccinic acid (R)-alpha-phenylethanammonium generated in a production process of mitiglinide calcium, and economic benefit is improved further.
5-AMINO-4-CARBAMOYL-PYRAZOLE COMPOUNDS AS SELECTIVE AND IRREVERSIBLE T790M OVER WT-EGFR KINASE INHIBITORS AND USE THEREOF????
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Paragraph 0197, (2016/03/13)
Disclosed are compounds of Formula (I), pharmaceutical compositions comprising the same, processes for the preparation thereof, and the use thereof.
A practical and efficient preparation of (S)-2-benzylsuccinic acid: A key acid synthon of KAD-1229
Liu, Jian-Chao,Yang, Yu-She,Ji, Ru-Yun
, p. 2633 - 2640 (2007/10/03)
This report describes a practical and an efficient synthesis of (S)-2-benzyl-succinic acid, which was employed as a key intermediate for hypoglycemic KAD-1229 by means of asymmetric alkylation of N-acylsultam. The condensation of D-(-)-camphorsultam with 3-phenylpropionyl chloride gave N-acylsultam 1. N-acylsultam 1 reacted with 1.1 equimolar amount of sodium amide base to form chiral enolate, followed by alkylation with tert-butyl bromoacetate to afford 2. Cleavage of ester and saponification with H 2O2-LiOH provided the desired compound 5 with excellent yield and high optical purity.
Diastereoselective conjugate addition of Grignard reagents to a homochiral fumaramide derived from Oppolzer's sultam
Reid, Gary P.,Brear, Kieron W.,Robins, David J.
, p. 793 - 801 (2007/10/03)
Conjugate addition of Grignard reagents to N,N′-fumaroylbis[(2R)- bornane-10,2-sultam] 1 occurred with moderate to high levels of diastereoselectivity. Diastereomeric excesses were estimated by analysis of the 1H NMR spectra of the succinamide mixtures and enantiomeric excesses from 19F NMR spectra of the bis Mosher esters of the diols produced by reductive cleavage of the succinamides. Saponification of the succinamides gave the corresponding (R)-succinic acids with ees up to 92% showing that addition of the Grignard reagents takes place selectively on the re-face of 1.
Preparation of (R)-(-)- and (S)-(+)-3-hydroxymethyl-1-tetralone tosylates, key intermediates in the synthesis of new CNS drugs, via resolution of precursors
Caro, Yolanda,Masaguer, Christian F.,Ravina, Enrique
, p. 381 - 387 (2007/10/03)
The preparation of (R)-(-)- and (S)-(+)-3-hydroxymethyl-1-tetralone tosylates, key intermediates in the synthesis of new CNS drugs in the aminobutyrophenone family, has been developed via classical resolutions or lipase-catalyzed kinetic resolution of one of their precursors.
(S)-3-methyl-2-phenylbutylamine, a versatile agent to resolve chiral, racemic carboxylic acids
Chikusa, Yasuo,Fujimoto, Taizo,Ikunaka, Masaya,Inoue, Toru,Kamiyama, Shunji,Maruo, Koichi,Matsumoto, Jun,Matsuyama, Keisuke,Moriwaki, Masafumi,Nohira, Hiroyuki,Saijo, Shigeya,Yamanishi, Masato,Yoshida, Kazuto
, p. 291 - 296 (2013/09/06)
(S)-Ibuprofen 2, (S)-ketoprofen 3, and (S)-naproxen 4 are all obtained by optical resolution of the respective racemates with (S)-3-methyl-2-phenylbutylamine (PBA) 1: (S)-2, 98.7% ee, 39.8% yield; (S)-3, 99.4% ee, 36.7% yield; (S)-4, 99.2% ee, 35.1% yield. (S)-PBA 1 is also useful in resolving other racemic carboxylic acids of pharmaceutical importance; (R)-2-hydroxy-4-phenylbutanoic acid (HPBA) 5, a key intermediate for ACE inhibitors such as benazapril 7, and (S)-2-benzylsuccinic acid (BSA) 6, a key intermediate for hypoglycemic KAD-1229 8, are obtained in 99% ee and 34.4% yield, and in 99% ee and 32.2% yield, respectively.
Enantioselective alkylation of lactams and lactones via lithium enolate formation using a chiral tetradentate lithium amide in the presence of lithium bromide
Matsuo, Jun-Ichi,Kobayashi, Shu,Koga, Kenji
, p. 9723 - 9726 (2007/10/03)
Enantioselective alkylation of lactams and lactones can be realized up to 98% ee by deprotonation with a chiral tetradentate lithium amide (4b) in the presence of lithium bromide, and subsequent alkylation with active alkylating agents in non-chelating solvents.
First asymmetric synthesis of the Kelatorphan-like enkephalinase inhibitor (1S,2R,2′S)-2-[2′-(N-hydroxycarbamoylmethyl)-3′- phenylpropionylamino]cyclohexane-1-carboxylic acid
Davies, Stephen G.,Dixon, Darren J.
, p. 2629 - 2634 (2007/10/03)
The first asymmetric synthesis of Kelatorphan-like enkephalinase inhibitor (1S,2R,2′S)-2-[2′-(N-hydroxycarbamoylmethyl)-3′- phenylpropionylamino]cyclohexane-1-carboxylic acid is achieved using lithium amide (R)-5 and pyrrolidinone auxiliary (R)-6; the pyrrolidinone auxiliary is used to create (2S)-benzylsuccinic acid derivative (S)-4 while lithium amide (R)-5 is used to synthesize tert-butyl (1S,2R)-2-aminocyclohexanecarboxylate 3.
