115626-59-0Relevant articles and documents
Asymmetric Synthesis of N-Substituted α-Amino Esters from α-Ketoesters via Imine Reductase-Catalyzed Reductive Amination
Yao, Peiyuan,Marshall, James R.,Xu, Zefei,Lim, Jesmine,Charnock, Simon J.,Zhu, Dunming,Turner, Nicholas J.
supporting information, p. 8717 - 8721 (2021/03/16)
N-Substituted α-amino esters are widely used as chiral intermediates in a range of pharmaceuticals. Here we report the enantioselective biocatalyic synthesis of N-substituted α-amino esters through the direct reductive coupling of α-ketoesters and amines employing sequence diverse metagenomic imine reductases (IREDs). Both enantiomers of N-substituted α-amino esters were obtained with high conversion and excellent enantioselectivity under mild reaction conditions. In addition >20 different preparative scale transformations were performed highlighting the scalability of this system.
SARTAN ANALOGUE
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Page/Page column 9; 10; 18; 21; 22, (2019/07/23)
The invention concerns a sartan analogue on basis of a sartan which sartan comprises an alkyl group or an alkoxy group, wherein the sartan analogue only differs from the sartan by a replacement of the alkyl group or the alkoxy group or replacement of a methyl residue or a hydrogen residue of the alkyl group or of the alkoxy group by a fluorine atom.
A method for synthesis of 1, 2 - pentanediol (by machine translation)
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Paragraph 0025; 0030; 0035; 0040; 0042; 0045; 0050, (2018/10/19)
The invention relates to the field of organic synthetic technology, in particular to a 1, 2 - pentanediol synthetic method, comprises the following steps: (1) heating the raw material-butyraldehyde, adjusting the pH after adding the hydrocyanic acid, obtained by the reaction of 2 - hydroxy pentanonitrile; (2) taking step (1) in 2 - hydroxy pentanonitrile, adding an alcohol as a solvent to stir and mix, add water to stir and mix, hydrogen chloride gas, in 5 °C the following reaction under the condition for a period of time, to continue the reaction temperature, after the reaction product after the neutralization reaction, centrifugal separation, obtained after the distillation is 2 - hydroxy valeric acid ester compound; (3) heating the step (2) in 2 - hydroxy valeric acid ester compound, under the effects of catalyst after hydrogenation reaction to obtain the 1, 2 - pentanediol. Using the synthesis method of the invention, the 1, 2 - pentanediol yield, and reduces the production cost. (by machine translation)
Enantioselective catalytic synthesis of ethyl mandelate derivatives using Rh(I)-NHC catalysts and organoboron reagents
Marques, Carolina S.,Burke, Anthony J.
, p. 628 - 632 (2013/07/19)
Herein we describe for the first time the enantioselective catalytic arylation of ethyl glyoxalate using phenylboron reagents and chiral rhodium(I)-NHC catalysts. KOtBu was the base of choice, along with tert-amyl alcohol as the solvent. A novel chiral bis-imidazolium salt was synthesized and evaluated for the first time in this catalytic transformation. Although moderate enantioselectivities (up to 34% ee) were obtained for the phenylation reaction, despite the excellent yields, very low enantioselectivities were obtained using other arylboronic acids with a variety of chiral rhodium(I)-NHC catalysts.
Expeditious and novel synthesis of α-hydroxyesters via rhodium-NHC catalyzed arylation of ethyl glyoxalate
Marques, Carolina S.,Burke, Anthony J.
experimental part, p. 7211 - 7216 (2012/09/05)
The rhodium-NHC catalyzed arylation reaction of ethyl glyoxalate with aryl and alkyl boronic acids provides an efficient method for the synthesis of α-hydroxyesters. A wide range of α-hydroxyesters (up to 12) were prepared in good to excellent yields. KOtBu was the base of choice, along with tert-amyl alcohol as the solvent. As far as we are aware, this is the first report of this catalytic arylation, using rhodium-NHC catalysts with this specific substrate type.
METHOD FOR PRODUCING OPTICALLY ACTIVE 2-HYDROXY ESTER AND NOVEL INTERMEDIATE COMPOUND
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Page/Page column 11, (2012/01/13)
Disclosed is a method for producing an optically active 2-hydroxy ester, comprising selectively esterifying one enantiomer of a racemic 2-hydroxy ester in a solvent containing a catalyst such as tetramisole or benzotetramisole, and a carboxylic acid anhydride, or a carboxylic acid anhydride and a carboxylic acid. In particular, in the case where the solvent contains a carboxylic acid anhydride, but does not contain a carboxylic acid, as the carboxylic acid anhydride, a carboxylic acid anhydride containing a tertiary or quaternary carbon atom in the a-position is used. On the other hand, in the case where the solvent contains a carboxylic acid anhydride and a carboxylic acid, as the carboxylic acid, a carboxylic acid containing a tertiary or quaternary carbon atom in the a-position is used.
Kinetic resolution of the racemic 2-hydroxyalkanoates using the enantioselective mixed-anhydride method with pivalic anhydride and a chiral acyl-transfer catalyst
Shiina, Isamu,Nakata, Kenya,Ono, Keisuke,Sugimoto, Masuhiro,Sekiguchi, Akihiro
supporting information; experimental part, p. 167 - 172 (2010/03/26)
A variety of optically active 2-hydroxyalkanoates and the corresponding 2-acyloxyalkanoates are produced by the kinetic resolution of racemic 2-hydroxyalkanoates by using achiral 2,2-diarylacetic acid with hindered carboxylic anhydrides as the coupling reagents. The combined use of diphenylacetic acid, pivalic anhydride, and (+)-(R)-benzotetramisole ((R)-BTM) effectively produces (S)-2-hydroxyalkanoates and (R)-2-acyloxyalkanoates from the racemic 2-hydroxyalkanoates (s-values = 47-202). This protocol directly provides the desired chiral 2-hydroxyalkanoate derivatives from achiral diarylacetic acid and racemic secondary alcohols that do not include the sec-phenethyl alcohol moiety by using the transacylation process to generate the mixed anhydrides from the acid components with bulky carboxylic anhydrides under the influence of the chiral acyl-transfer catalyst. The transition state that provides the desired (R)-2-acyloxyalkanoate from (R)-2-hydroxyalkanoate included in the racemic mixture is disclosed by DFT calculations, and the structural features of the transition form are also discussed.
Stereoselective reduction of carbonyl compounds with actinomycete: Purification and characterization of three α-keto ester reductases from Streptomyces avermitilis
Ishihara, Kohji,Kato, Chiaki,Yamaguchi, Hitomi,Iwai, Rieko,Yoshida, Momoko,Ikeda, Natsumi,Hamada, Hiroki,Masuoka, Noriyoshi,Nakajima, Nobuyoshi
body text, p. 3249 - 3257 (2009/04/10)
We achieved the purification of three α-keto ester reductases (Streptomyces avermitilis keto ester reductase, SAKERs-I, -II, and -III) from Streptomyces avermitilis NBRC14893 whole cells. The molecular masses of the native SAKERs-I, -II, and -III were estimated to be 72, 38, and 36 kDa, respectively, by gel filtration chromatography. The subunit molecular masses of SAKERs-I, -II, and -III were also estimated to be 32, 32, and 34 kDa, respectively, by SDS-polyacrylamide gel electrophoresis. The purified SAKERs-II and -III showed a reducing activity for α-keto esters (in particular, for ethyl pyruvate). SAKER-I showed a high reducing activity not only toward the α- and β-keto esters, but also toward α-keto acid. The N-terminal region amino acid sequences of SAKERs-I, -II, and -III were identical to that of a putative oxidoreductase, SAV2750, a putative oxidoreductase, SAV1849, and a putative oxidoreductase, SAV4117, respectively, hypothetical proteins coded on the S. avermitilis genome.
PROCESS FOR PRODUCTION OF 2-HYDROXY ESTERS
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Page/Page column 14, (2010/11/30)
The invention provides an easy and simple process for the production of 2-hydroxy esters from cyanohydrins, specifically, a process for the production of 2-hydroxy esters represented by the general formula (1) (exclusive of ethyl 2-hydroxy-4-phenylbutyrate), characterized by introducing an acid into a mixture comprising a cyanohydrin represented by the general formula (2), an alcohol, an organic solvent and water: [Chemical formula 1] R1 -CH(OH)-COOR2 (1) R1 -CH(OH)(CN) (2) wherein R1 is hydrogen, a substituted or unsubstituted aliphatic hydrocarbon group which has 1 to 12 carbon atoms and may contain oxygen, sulfur, or nitrogen, a substituted or unsubstituted alicyclic hydrocarbon group which has 3 to 12 carbon atoms and may contain oxygen, sulfur, or nitrogen, or a substituted or unsubstituted aryl or aralkyl group which has 3 to 14 carbon atoms and may contain oxygen, sulfur, or nitrogen; and R2 is alkyl which has 1 to 12 carbon atoms and may contain oxygen, sulfur, or nitrogen.
The bakers' yeast reductions of α- and β-keto ester derivatives in the presence of a sulfur compound
Hayakawa, Ryuuichirou,Nozawa, Kazumi,Kimura, Kimihiko,Shimizu, Makoto
, p. 7519 - 7528 (2007/10/03)
Improvement of the enantioselectivity and enhancement of the reactivity were achieved in the bakers' yeast reduction of the α- and β-keto ester derivatives by the addition of a sulfur compound. High enantioselectivity in the bakers' yeast reduction of keto esters was accomplished by using combination of an addition of a sulfur compound with an appropriate selection of the alcohol part of the ester.