CAS: 769195-26-8; Methyl 3-Oxo-4-(2,4,5-Trifluorophenyl)Butanoate

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CAS号38330-80-2 丙二酸单甲酯钾盐 | CAS号209995-38-0 2,4,5-三氟苯乙酸 | CAS号764667-64-3 5-[1-羟基-2-(2,4,... | CAS号67-56-1 甲醇 | CAS号868071-17-4 (3S)-2',4',5'-三... | CAS号654671-77-9 磷酸西他列汀 | CAS号486460-00-8 (3R)-N-叔丁氧羰基-3-... | CAS号486460-32-6 西他列汀

📜5-[1-羟基-2-(2,4,5-三氟苯基)亚乙基]-2,2-二甲基-1,3-二氧六环-4,6-二酮 以 甲醇 作为反应溶剂,以75 %的收率获得产物3-氧代-4-(2,4,5-三氟苯基)丁酸甲酯
参考文献:β-氨基-N-酰腙的立体化学见解及其对 Dpp-4 抑制的影响
标题:β-氨基-N-酰腙的立体化学见解及其对 Dpp-4 抑制的影响
摘要:二肽基肽酶 Iv (Dpp-4) 是调节多个重要生物过程的关键酶,众所周知,格列汀是治疗 2 型糖尿病 (T2Dm) 的现代有效方法.然而,仍然需要能够控制与 T2Dm 慢性并发症相关的炎症过程的新一代 Dpp-4 抑制剂.在这种情况下,我们在这里报告了新型 β-氨基-N-酰腙的分子建模设计,它们的外消旋合成,手性拆分,理化性质的测定及其 Dpp4 抑制效力.理论和实验方法使我们能够提出初步的 Sar,并确定 Lassbio-2124 (6) 作为 Dpp-4 抑制的新先导化合物,具有非常好的理化性质,非常好的非常好比例,可扩展的合成和抗糖尿病作用.概念验证模型.这些发现为开发新一代 Dpp-4 抑制剂提供了一个有趣的起点,可用于治疗 T2Dm 和合并症.
DOI:10.1039/d4Ra00450G

专利信息

专利号:US-2024035023-A1
优先权日:2022-06-24
标题 :Computer implemented method for engineering fluorinase enzymes for synthesis of fluorophenyl compounds
发明人：R PRAVIN KUMAR; G GLADSTONE SIGAMANI; L ROOPA; B K NAVEEN; SHETTY ANUJ J; M LIKITH
权利人:KCAT ENZYMATIC PRIVATE LTD
摘要:The present invention discloses a computer-implemented method for engineering fluorinase enzymes towards the synthesis of fluorophenyl compounds. Limited or no mechanistic details of fluorinase enzymes have hindered progress in understanding their catalytic mechanisms for synthesizing synthetic organofluorine compounds. Through a comprehensive computational screening process, specific methionine-sulfonium phenyl substrates, including [(3S)-3-amino-3-carboxypropyl][2,5-difluoro-4-(4-methoxy-2,4-dioxobutyl)phenyl]methylsulfonium, were designed and optimized using quantum chemical optimization techniques. This methodology uncovers crucial information on F— ion attack conformation and the catalytic mechanism of the substrate, leading to the formation of Methyl 3-oxo-4-(2,4,5-trifluorophenyl)butanoate. Furthermore, a protein sequence and 3D modeling-based enzyme screening process was employed to identify the most suitable enzyme for this substrate. The identified enzyme was then engineered using the mechanistic insights gained from the studies, resulting in improved substrate scope, stability and catalytic efficiency. This computer-based approach offers an efficient and precise alternative to traditional trial-and-error methods, advancing the field towards the successful synthesis fluorophenyl compounds.

专利号:US-8846916-B2
优先权日:2009-05-11
标题:Sitagliptin synthesis
发明人：GORE VINAYAK GOVIND; GADAKAR MAHESHKUMAR; BHOSLE PRIYANKA; SHINDE SURESH
权利人:GORE VINAYAK GOVIND; GADAKAR MAHESHKUMAR; BHOSLE PRIYANKA; SHINDE SURESH; GENERICS UK LTD
摘要:The present invention relates to novel processes for the preparation of enantiomerically enriched β-amino acid derivatives such as β-amino esters useful for the synthesis of enantiomerically enriched biologically active molecules such as sitagliptin. The key step involves the resolution of the racemate with mandelic acid.

专利号:WO-2009064476-A1
优先权日:2007-11-13
标 题 :Preparation of sitagliptin intermediate
发明人：PERLMAN NURIT; ETINGER MARINA; NIDDAM-HILDESHEIM VALERIE; ABRAMOV MILI
权利人:TEVA PHARMA; TEVA PHARMA; PERLMAN NURIT; ETINGER MARINA; NIDDAM-HILDESHEIM VALERIE; ABRAMOV MILI
摘要:Intermediate compounds in the synthesis of Sitagliptin, 3-amino-4-(2,4,5- trifluorophenyl)but-2-enoic acid alkyl ester, and amino protected-3-amino-4-(2,4,5- trifluorophenyl)but-2-enoic acid alkyl ester, and the stereoselective reduction of these compound to give Synthon I, or the amino-protected Synthon I, are provided.

专利号:US-2009123983-A1
优先权日:2007-10-03
标 题:Processes for preparing an intermediate of sitagliptin via enzymatic reduction
发明人：NIDDAM-HILDESHEIM VALERIE
权利人:NIDDAM-HILDESHEIM VALERIE
摘要:The invention provides enzymatic reduction processes for the preparation of 4-(2,4,5-trifluorophenyl)-3-hydroxybutanoate, particularly, (S)-methyl 4-(2,4,5-trifluorophenyl)-3-hydroxybutanoate, a key intermediate in the synthesis of Sitagliptin, and the (S)- and (R)-enantiomers of methyl 4-(2,4,5-trifluorophenyl)-3-hydroxybutanoate in high enantiomeric purity.

专利号:US-2009192326-A1
优先权日:2007-11-13
标题 :Preparation of sitagliptin intermediate
发明人：PERLMAN NURIT; ETINGER MARINA; NIDDAM-HILDESHEIM VALERIE; ABRAMOV MILI
权利人:PERLMAN NURIT; ETINGER MARINA; NIDDAM-HILDESHEIM VALERIE; ABRAMOV MILI
摘要:Intermediate compounds in the synthesis of Sitagliptin, 3-amino-4-(2,4,5-trifluorophenyl)but-2-enoic acid alkyl ester, and amino protected-3-amino-4-(2,4,5-trifluorophenyl)but-2-enoic acid alkyl ester, and the stereoselective reduction of these compound to give Synthon I, or the amino-protected Synthon I, are provided.

专利号:WO-2013114173-A1
优先权日:2012-01-30
标题:A novel process for the preparation of sitagliptin
发明人：MALLELA SAMBHU PRASAD SARMA; HAVALE SHRIKANT HANUMANTAPPA; BODDEPALLI NAGABHUSHANA RAO; GUNJI NAGARJUNA; MOKKAPATI BHAVANI SANKAR
权利人:SMILAX LAB LTD; MALLELA SAMBHU PRASAD SARMA; HAVALE SHRIKANT HANUMANTAPPA; BODDEPALLI NAGABHUSHANA RAO; GUNJI NAGARJUNA; MOKKAPATI BHAVANI SANKAR
摘要:The present invention is directed to a process for the preparation of enantiomerically enriched β-amino acid derivatives which are important chiral building blocks and intermediates in pharmaceuticals. More specifically, the invention pertains to a novel process for practically convenient and economically producing enantiomerically enriched β-amino acid derivatives which are useful for the synthesis of amide inhibitors of dipeptidyl peptidase IV like Sitagliptin, which have been used to treat type 2 diabetes.