C:Corrosive;
5856-62-2Relevant articles and documents
A mild and highly efficient synthesis of chiral N-dichloroacetyl-4-ethyl-1, 3-oxazolidines
Zhao, Li-Xia,Fu, Ying,Ye, Fei,Gao, Shuang
, p. 943 - 946 (2012)
Chiral 2-amino-butanols (4 and 5) were obtained via the isolation of diastereomeric salt. Then, chiral compounds (6-9) were synthesized by a sequential procedure involving condensation of chiral 2-amino-butanol with ketone and dichloroacetyl chloride. All the compounds were characterized by IR, 1H NMR, 13C NMR, and element analysis. The absolute configurations of (S)-8 was determined by X-ray crystallography.
Preparation, characterization and performance evaluation of separation of alcohol using crosslinked membrane materials
Ingole, Pravin G.,Thakare, Neha R.,Kim, Keehong,Bajaj, Hari C.,Singh, Kripal,Lee, Hyungkeun
, p. 4018 - 4024 (2013)
In the present study the glutaraldehyde-crosslinked chitosan membrane (GXCM) was prepared and chiral resolution of (R,S)-2-amino-1-butanol (2A1B) was performed. The membrane was analyzed by Attenuated Total Reflectance Fourier Transform Infrared Spectroscopy (ATR-FTIR) for its chemical composition. The morphology of the membrane was studied by Scanning Electron Microscopy (SEM) and correlated with membrane performance. The performance of the GXCM membrane was quantified by performing chiral resolution of (R,S)-2-amino-1-butanol in pressure driven separation and the influences of permeation parameters such as operating pressure, concentration of feed solutions, concentration of copper(ii) ions were investigated to understand the chiral selectivity of the membrane. The optical resolution of (R,S)-2-amino-1-butanol racemic mixture, 92% of enantiomeric excess (% ee) was achieved. The separation ability of the above crosslinked membrane was also investigated, and a separation factor of up to 5.6 was achieved.
Enantioselective Cascade Biocatalysis for Deracemization of Racemic β-Amino Alcohols to Enantiopure (S)-β-Amino Alcohols by Employing Cyclohexylamine Oxidase and ω-Transaminase
Zhang, Jian-Dong,Chang, Ya-Wen,Dong, Rui,Yang, Xiao-Xiao,Gao, Li-Li,Li, Jing,Huang, Shuang-Ping,Guo, Xing-Mei,Zhang, Chao-Feng,Chang, Hong-Hong
, p. 124 - 128 (2020/09/21)
Optically active β-amino alcohols are very useful chiral intermediates frequently used in the preparation of pharmaceutically active substances. Here, a novel cyclohexylamine oxidase (ArCHAO) was identified from the genome sequence of Arthrobacter sp. TYUT010-15 with the R-stereoselective deamination activity of β-amino alcohol. ArCHAO was cloned and successfully expressed in E. coli BL21, purified and characterized. Substrate-specific analysis revealed that ArCHAO has high activity (4.15 to 6.34 U mg?1 protein) and excellent enantioselectivity toward the tested β-amino alcohols. By using purified ArCHAO, a wide range of racemic β-amino alcohols were resolved, (S)-β-amino alcohols were obtained in >99 % ee. Deracemization of racemic β-amino alcohols was conducted by ArCHAO-catalyzed enantioselective deamination and transaminase-catalyzed enantioselective amination to afford (S)-β-amino alcohols in excellent conversion (78–94 %) and enantiomeric excess (>99 %). Preparative-scale deracemization was carried out with 50 mM (6.859 g L?1) racemic 2-amino-2-phenylethanol, (S)-2-amino-2-phenylethanol was obtained in 75 % isolated yield and >99 % ee.
Selective hydrogenation of primary amides and cyclic di-peptides under Ru-catalysis
Subaramanian, Murugan,Sivakumar, Ganesan,Babu, Jessin K.,Balaraman, Ekambaram
supporting information, p. 12411 - 12414 (2020/10/30)
A ruthenium(II)-catalyzed selective hydrogenation of challenging primary amides and cyclic di-peptides to their corresponding primary alcohols and amino alcohols, respectively, is reported. The hydrogenation reaction operates under mild and eco-benign conditions and can be scaled-up.
Data mining of amine dehydrogenases for the synthesis of enantiopure amino alcohols
Guo, Jinggong,Li, Jun-Kuan,Ma, Jun-An,Miao, Yuchen,Qu, Ge,Sun, Zhoutong,Wang, Hongyue
, p. 5945 - 5952 (2020/10/08)
Chiral amino alcohols are essential building blocks for the pharmaceutical industry, and are widely present in natural and synthetic bioactive compounds. Amine dehydrogenases (AmDHs) can asymmetrically reduce prochiral ketones with low-cost ammonia to chiral amines and water as by-products, using NAD(P)H as a cofactor under mild conditions, but hydroxy ketones with formation of chiral hydroxy amines have rarely been investigated. In this study, six new bacterial AmDHs derived from amino acid dehydrogenases (AADHs) were identified by data mining, and five out of the six enzymes were able to efficiently reduce 1-hydroxybutan-2-one (1a) to (S)-2-aminobutan-1-ol ((S)-2a) with 19-99% conversions and 99% ee. The five AmDHs were purified and biochemically characterized for reductive amination activity towards substrate 1a with the optimal pH at 8.5 or 9.0 and the optimal temperature at 45 °C, 50 °C or 55 °C, and provided reductive amination of a broad range of prochiral α-hydroxy ketones, and even of a model β-hydroxy ketone leading to β-hydroxy amine with 99% ee. Our study expands the toolbox of AmDHs in the synthesis of chiral amino alcohols.
Asymmetric ring opening of racemic epoxides for enantioselective synthesis of (S)-β-amino alcohols by a cofactor self-sufficient cascade biocatalysis system
Zhang, Jian-Dong,Yang, Xiao-Xiao,Jia, Qiao,Zhao, Jian-Wei,Gao, Li-Li,Gao, When-Chao,Chang, Hong-Hong,Wei, Wen-Long,Xu, Jian-He
, p. 70 - 74 (2019/01/10)
A novel one-pot epoxide hydrolase/alcohol dehydrogenase/transaminase cascade process for the asymmetric ring opening of racemic epoxides to enantiopure β-amino alcohols is reported. The product (S)-β-amino alcohols were obtained in 97-99% ee and 79-99% conversion from readily available racemic epoxides.
Chiral resolution method for preparing L-2-amino-1-butanol
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Paragraph 0015-0016, (2019/10/04)
The invention relates to a chiral resolution method for preparing L-2-amino-1-butanol. The method concretely comprises the following steps: a) carrying out multi-step derivatization on (1S,2S)-1,2-cyclohexanediamine used as a precursor to prepare a target chiral resolving agent; b) dissolving a racemic compound 2-amino-1-butanol in an ethanol/water mixed solution, and mixing the obtained solution with equimolar amounts of the chiral resolving agent and copper chloride to precipitate a blue solid; and c) carrying out reduced pressure rotary evaporation to remove the ethanol in the mixed solution, extracting with ethyl acetate, concentrating obtained filtrate, and performing vacuum drying to obtain the optically pure levo compound 2-amino-1-butanol with the ee value reaching up to 99.0% or more. The chiral resolving agent has the advantages of simple synthesis process, mild reaction conditions, high optical purity of the product, cost saving, and suitableness for industrial resolution.
Continuous-flow protocol for the synthesis of enantiomerically pure intermediates of anti epilepsy and anti tuberculosis active pharmaceutical ingredients
Aguiar, Renata M.,Le?o, Raquel A. C.,Mata, Alejandro,Cantillo, David,Kappe, C. Oliver,Miranda, Leandro S. M.,De Souza, Rodrigo O. M. A.
supporting information, p. 1552 - 1557 (2019/02/14)
Continuous-flow production of chiral intermediates plays an important role in the development of building blocks for Active Pharmaceutical Ingredients (APIs), being α-amino acids and their derivatives widely applied as building blocks. In this work we developed two different strategies for the synthesis of intermediates used on the synthesis of levetiracetam/brivaracetam and ethambutol. The results obtained show that methionine methyl ester can be continuously converted to the desired ethambutol intermediate by RANEY Nickel dessulfurization/reduction strategy whereas levetiracetam/brivaracetam intermediates could be synthesized by both RANEY Nickel (without H2) and Pd/C-H2 approach or by photochemical desulfurization.
Enantioselective Synthesis of Chiral Vicinal Amino Alcohols Using Amine Dehydrogenases
Chen, Fei-Fei,Cosgrove, Sebastian C.,Birmingham, William R.,Mangas-Sanchez, Juan,Citoler, Joan,Thompson, Matthew P.,Zheng, Gao-Wei,Xu, Jian-He,Turner, Nicholas J.
, p. 11813 - 11818 (2019/12/02)
Chiral vicinal amino alcohols are an important motif found in many biologically active molecules. In this study, biocatalytic reductive amination of α-hydroxy ketones with ammonia was investigated using engineered amine dehydrogenases (AmDHs) derived from the leucine amino acid dehydrogenase (AADH) from Lysinibacillus fusiformis. The AmDHs thus identified enabled the synthesis of (S)-configured vicinal amino alcohols from the corresponding α-hydroxy ketones in up to 99% conversions and >99% ee. One of the AmDH variants was used to prepare a key intermediate for the antituberculosis pharmaceutical ethambutol.
Method for synthesizing S-(+)-2-aminobutanol by catalyzing hydrogenation of S-(+)-2-aminobutyric acid
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Paragraph 0046-0049, (2017/09/01)
The invention relates to a method for synthesizing S-(+)-2-aminobutanol by catalyzing hydrogenation of S-(+)-2-aminobutyric acid. According to the method, a product S-(+)-2-aminobutanol is prepared from S-(+)-2-aminobutyric acid through catalytic hydrogenation under acidic conditions by taking water as a solvent and Ru-X-Y/AC as a catalyst; X represents one of Pt and Pd in the Ru-X-Y/AC catalyst, Y represents one of Cu, Mn and Fe, and the loading amounts of three metals of Ru, X and Y respectively are 3%t%-5wt%, 0.1wt%-1wt% and 0.1wt%-1wt%. According to the method, the relatively high yield can be realized at a relatively low pressure and temperature, the reaction time is greatly shortened, the energy consumption is reduced, and the catalyst is good in stability and can be repeatedly used.
