- α-Methoxy-α-trifluoromethylpropionic Acid (MTPr). A New Chiral Derivatizing Reagent for GC Separation of Enantiomeric Amino Acids
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A title homochiral acid has been synthesized and shown to be an efficient chiral derivatizing reagent for capillary gas chromatographic separation of emnantiomeric amino acids at considerably low column temperature.
- Yasuhara, Fujiko,Takeda, Masayuki,Ochiai, Yoshiro,Miyano, Sotaro,Yamaguchi, Shozo
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Read Online
- Method for synthesizing 2-hydroxy-2-(fluoro-containing methyl) propionic acid
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The invention provides a method for synthesizing 2-hydroxy-2-(fluoro-containing methyl) propionic acid. The method takes 2-methylacetoacetic ester as a starting raw material, and the 2-hydroxy-2-(fluoro-containing methyl) propionic acid is obtained after an alpha-substitution reaction, a Baeyer-Villiger oxidation reaction, saponification, and an acidification reaction. The raw materials of the reaction route are easily available, the reaction conditions are safe and mild, and the method is suitable for industrial production.
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Paragraph 0017
(2018/10/19)
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- 2-Trifluoromethyl-2-Hydroxypropionamide Derivatives as Novel Reversal Agents of ABCG2 (BCRP)-Mediated Multidrug Resistance: Synthesis and Biological Evaluations
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It has been postulated that one of the biggest impediments to a successful chemotherapy is the phenomena of multidrug resistance (MDR) in cancer cells. One of the main mechanisms of MDR is overexpression of the ATP-binding cassette (ABC) transporters in c
- Kathawala, Rishil J.,Li, Tianwen,Yang, Danwen,Guo, Hui-Qin,Yang, Dong-Hua,Chen, Xiang,Cheng, Changmei,Chen, Zhe-Sheng
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p. 2420 - 2429
(2017/06/13)
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- Efficient preparation of both enantiomers of 3,3,3-trifluoro-2-hydroxy-2- methylpropanoic acid catalyzed by Shinella sp. R-6 and Arthrobacter sp. S-2
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Several microorganisms that can enantioselectively hydrolyze 3,3,3-trifluoro-2-hydroxy-2-methylpropanamide have been isolated from soil samples. These strains were capable of growing in a medium containing 3,3,3-trifluoro-2-hydroxy-2-methylpropanamide as the sole nitrogen source. Among them, Shinella sp. R-6 was identified as a strain capable of exhibiting R-selective hydrolysis activity, while Arthrobacter sp. S-2 was capable of exhibiting S-selective hydrolysis activity. The preparation of both enantiomers of 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid via the two-step whole-cell reaction was investigated using these two strains.
- Fuhshuku, Ken-Ichi,Watanabe, Shunsuke,Nishii, Tetsuro,Ishii, Akihiro,Asano, Yasuhisa
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p. 115 - 119
(2014/03/21)
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- Chirality-dependent sublimation of α-(trifluoromethyl)-lactic acid: Relative vapor pressures of racemic, eutectic, and enantiomerically pure forms, and vibrational spectroscopy of isolated (S,S) and (S,R) dimers
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A mass-spectrometric determination of the sublimation pressure diagram of α-(trifluoromethyl)-lactic acid as a function of its enantiomeric composition at 293 K shows that the racemic crystals have a 38 ± 15 % higher volatility than the enantiomerically p
- Albrecht, Merwe,Soloshonok, Vadim A.,Schrader, Lena,Yasumoto, Manabu,Suhm, Martin A.
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experimental part
p. 495 - 504
(2010/05/17)
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- Method for controlled polymerization of o-carboxy anhydrides derived from alpha-hydroxy acids
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The invention concerns a method for preparing poly(-hydroxy acids), the polymerization reaction being performed in controlled manner in the presence of a catalytic system including a base, said base being a 5- or 6-membered aromatic heterocycle comprising
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Page/Page column 15
(2010/11/28)
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- Oxazolones as potent inhibitors of 11β-hydroxysteroid dehydrogenase type 1
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2,5,5-Trisubstituted oxazolones were identified as potent inhibitors of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1). The synthesis, structure-activity relationship and metabolic stability of these compounds are presented.
- Sutin, Lori,Andersson, Soeren,Bergquist, Lars,Castro, Victor M.,Danielsson, Eva,James, Stephen,Henriksson, Martin,Johansson, Lars,Kaiser, Christina,Flyren, Katarina,Williams, Meredith
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p. 4837 - 4840
(2008/02/11)
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- Synthetic application of 3,3-dichloro-1, 1, 1-trifluoroacetone (DCTFA) and 3,3,3-trichloro-1, 1, 1-trifluoroacetone (TCTFA) for trifluorolactic acid derivatives
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Synthetic application of 3,3-dichloro-1,1,1-trifluoroacetone (DCTFA) and 3,3,3-trichloro-1,1,1-trifluoroacetone (TCTFA) for industrially important trifluorolactic acid derivatives is described. Trifluorolactic acid was obtained by hydrolysis of DCTFA unde
- Ishii, Akihiro,Kanai, Masatomi,Yasumoto, Manabu,Inomiya, Kenjin,Kuriyama, Yokusu,Katsuhara, Yutaka
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p. 567 - 571
(2007/10/03)
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- Optically active fluorine-containing compounds and processes for their production
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An optically active fluorine-containing compound represented by the following formula (1) or (2) wherein A is an oxygen atom, a sulfur atom or an NH group, and R1 selected from a variety of organic group, is used in the preparation of (S)- or (R)-3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid.
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- Substituted N-phenyl 2-hydroxy-2-methyl-3,3,3-trifluoropropanamide derivatives which elevate pyruvate dehydrogenase activity
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A compound of formula (I) wherein: n is 1 or 2; R 1 is chloro, fluoro, bromo, methyl or methoxy; R 2 is as defined within; R 3 is as defined within; and R 4 is hydrogen or fluoro; or a pharmaceutically acceptable salt or an in vivo hydrolysable ester thereof is described. The use of compounds of formula (I) in the production of an elevation of PDH activity in a warm-blooded animal such as a human being are also described. Pharmaceutical compositions, methods and processes for preparation of compounds of formula (I) are detailed. STR1
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Page column 51
(2010/02/05)
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- Benzenesulfonamide-derivatives and their use as medicaments
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Compounds of formula (I), pharmaceutically acceptable salts or in vivo hydrolysable esters thereof, wherein: Ring X is phenyl or a six membered heteroaryl ring containing one or two ring nitrogens where said nitrogens are optionally oxidised to form the N
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Page column 73
(2010/11/30)
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- Selection, purification, characterisation, and cloning of a novel heat-stable stereo-specific amidase from Klebsiella oxytoca, and its application in the synthesis of enantiomerically pure (R)- and (S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionic acids and (S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionamide
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We isolated, characterised, and cloned an enantio-specific amidase from Klebsiella oxytoca and used it to resolve (R,S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionamide, giving (R)3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid and (S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionamide. The (S)-amide could then be hydrolysed chemically to (S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid. The process can therefore be adapted to produce both (R)-and (S)-enantiomers of 3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid, or (S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionamide. The biocatalytic step is part of a combined chemical and biocatalytic route that starts from ethyl trifluoroacetoacetate. The products typically have a purity of greater than 98% and ee values of essentially 100% after isolation. The process has been used to produce 100-g amounts of the (S)-acid, and successfully scaled up to produce 100-kg amounts of the (R)-acid, with the biotransformation carried out at the 1500-L scale.
- Shaw, Nicholas M.,Brieden, Walter,De Riedmatten, Patricia,Roduit, Jean-Paul,Zimmermann, Bertin,Neumueller, Roman,Naughton, Andrew,Robins, Karen,Tinschert, Andreas,Schmid, Evelyne,Hischier, Marie-Louise,Venetz, Veronika,Werlen, Josef,Zimmermann, Thomas
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p. 497 - 504
(2013/09/06)
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- Process for producing optically active 3,3,3-Trifluoro-2-Hydroxy-2-Methylpropionic acid, and salt thereof
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There are disclosed are a diastereomer salt of formula (1): a process for producing the same, a process for producing optically active 3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid of formula (2′): a novel optically active amine compound of formula (4): a novel optically active amine compound of formula (8): an imine compound of formula (7) or (11):
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- Use of compounds for the elevation of pyruvate dehydrogenase activity
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The use of compounds of the formula (I), and salts thereof; and pharmaceutically acceptable in vivo cleavable prodrugs of said compound of formula (I); and pharmaceutically acceptable salts of said compound or said prodrugs: wherein: Ring C is phenyl or a carbon linked heteroaryl ring substituted as defmed within; R1is an ortho substituent as defined within; n is 1 or 2; A—B is a linking group as defined within; R2and R3are as defined within; R4is hydroxy, hydrogen, halo, amino or methyl; in the manufacture of a medicament for use in the elevation of PDH activity in warm-blooded animals such as humans is described. Pharmaceutical compositions, methods and processes for preparation of compounds of formula (I) are also described.
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- Tricyclic compounds
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The present invention provides tricyclic compounds which are useful for the treatment of pollakiuria and urinary incontinence and which are represented by general formula (I): (whereinR1 represents hydrogen, substituted or unsubstituted lower a
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- The synthesis of (R)- and (S)-α-trifluoromethyl-α-hydroxycarboxylic acids via enzymatic resolutions
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Kinetic resolution of 1, 1, 1-trifluoro-2-alkanone cyanohydrin acyl derivatives with Candida rugosa lipase afforded the remaining (R)-enantiomer in high selectivity (E from 30 to >200). Candida rugosa lipases from several suppliers were compared and found
- Konigsberger, Kurt,Prasad, Kapa,Repic, Oljan
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p. 679 - 687
(2007/10/03)
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- Tricyclic compounds
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The present invention relates to tricyclic compounds represented by general formula (I) which are useful as therapeutic agents for urinary incontinence: STR1 wherein R1 represents hydrogen and the like; --X1 --X2 --X3
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- α-TRIFLUOROMETHYL-α-HYDROXY CARBOXYLIC ACIDS
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The methyl esters of α-trifluoromethyl-α-hydroxy carboxylic acids were obtained by the reaction of methyl trifluoropyruvate with organometallic reagents (Cd, Mg, Zn).The characteristic features of the reactions in relation to the nature of the alkylating agent were demonstrated.
- Soloshonok, V. A.,Gerus, I. I.,Yagupol'skii, Yu. L.,Kukhar', V. P.
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p. 1298 - 1303
(2007/10/02)
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