CAS: 881995-73-9; Methyl (R)-3-((Tert-Butoxycarbonyl)Amino)-4-(2,4,5-Trifluorophenyl)Butanoate

该化合物是合成有机化合物,其复杂结构特征包括一种苯丁酸基酸基,一个三氟基甲基组和一个甲基酯功能组.该化合物具有一个手性中心的特点,表明它以对应形式存在,可以显示不同的生物活动.三氟甲基组的存在会增强它的脂性,并可能影响其药用植物特性,使其有可能在药用化学中发挥作用.二甲基乙氧基碳基化合物组是氨基功能的保护性组,在合成途径中至关重要.

结构式图片

物理性质

MSDS等安全信息

上下游产品

(2Z)-3-amino-4-(2,4,5-trifluorophenyl)but-2-enoic acid methyl ester tert-butyl dicarbonatedi-tert-butyl dicarbonate (R)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid methyl ester 4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid (R)-[3-oxo-3-pyrazolidin-1-yl-1-(2,4,5-trifluorobenzyl)propyl]carbamic acid tert-butyl ester (R)-[3-oxo-3-(tetrahydropyridazin-1-yl)-1-(2,4,5-trifluorobenzyl)propyl]carbamic acid tert-butyl ester (R)-[3-[1,2]diazepan-1-yl-3-oxo-1-(2,4,5-trifluorobenzyl)propyl]carbamic acid tert-butyl ester

合成工艺路线路线简述

  • 1234321-77-7 = 881995-73-9
    反应条件:1.1 Reagents: Tetrabutylammonium Iodide,Hydrogen Catalysts: Nickel Acetate,(R,R)-Methyl-Duphos Solvents: Methanol; 30 H,30 Bar,70 °C1.2 Reagents: Ethyl Acetate
    标题:Nickel-Catalyzed Asymmetric Hydrogenation For The Synthesis Of A Key Intermediate Of Sitagliptin
    作者:Sudhakaran,Shana; Et Al
    参考文献:Chemistry - An Asian Journal 日期:2022 卷标:17(1)]

    24424-99-5 + 881995-69-3 = 881995-73-9
    反应条件:1.1 Reagents: 4-(Dimethylamino)Pyridine Solvents: Acetonitrile; 10 Min1.2 Solvents: Acetonitrile; 4 H,Cooled1.3 Reagents: Water
    标题:Synthesis Of Type 2 Anti-Diabetic Drug Sitagliptin Phosphate
    作者:Lu,Cheng-Lin; Et Al
    参考文献:Zhongguo Xinyao Zazhi 日期:2014 卷标:23(13) 页码:1574-1578]

    24424-99-5 + 881995-70-6 = 881995-73-9
    反应条件:1.1 Reagents: Hydrogen Catalysts: Di-μ-Chlorobis[(1,2,5,6-η)-1,5-Cyclooctadiene]Dirhodium,(2R)-1-[(1R)-1-[bis(1,1-Dimethylethyl)Phosphino]Ethyl]-2-(Diphenylphosphino)Ferr... Solvents: Methanol; 24 H,90 Psi,30 °C
    标题:Application Of The Asymmetric Hydrogenation Of Enamines To The Preparation Of A Beta-Amino Acid Pharmacophore
    作者:Kubryk,Michele; Et Al
    参考文献:Tetrahedron: Asymmetry 日期:2006 卷标:17(2) 页码:205-209]

    24424-99-5 = 881995-73-9
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Dihydroxide Solvents: Methanol; Overnight,5 Atm,Rt1.2 Reagents: Hydrochloric Acid Solvents: Dichloromethane,Water; 10 Min,Rt1.3 Reagents: Potassium Carbonate Solvents: Water; Neutralized1.4 Reagents: Triethylamine Solvents: Dichloromethane; 8 H,Rt
    标题:The Asymmetric Synthesis Of Sitagliptin,A Selective Dipeptidyl Peptidase Iv Inhibitor For The Treatment Of Type 2 Diabetes
    作者:Liu,Feng; Et Al
    参考文献:Journal Of Chemical Research 日期:2010 卷标:34(4) 页码:230-232]

    24424-99-5 + 881995-69-3 = 881995-73-9
    反应条件:1.1 Catalysts: 4-(Dimethylamino)Pyridine Solvents: Ethyl Acetate; 10 Min,Rt1.2 Solvents: Acetone; 4 H,Cooled
    标题:Synthesis Of The Key Intermediate Of Type 2 Diabetes Drug Sitagliptin
    作者:Liu,Ying-Shuai; Et Al
    参考文献:Zhongguo Yaowu Huaxue Zazhi 日期:2012 卷标:22(5) 页码:360-363]

    486460-00-8 = 881995-73-9
    反应条件:1.1 Reagents: Thionyl Chloride Solvents: Methanol; 0 °C; 0 °C -> Reflux; 20 H,Reflux
    标题:Enantiospecific Synthesis Of (R)-3-Amino-4-(2,4,5-Trifluorophenyl)Butanoic Acid Using (S)-Serine As A Chiral Pool
    作者:Kose,Aytekin; Et Al
    参考文献:Helvetica Chimica Acta 日期:2015 卷标:98(2) 页码:260-266]

    24424-99-5 = 881995-73-9
    反应条件:1.1 Reagents: Hydrogen,Hydrochloric Acid Catalysts: Palladium Solvents: Diethyl Ether,Ethanol; 4 H,5 Atm,Rt1.2 Reagents: Hydrochloric Acid Solvents: Dichloromethane,Water; 10 Min,Rt1.3 Reagents: Potassium Carbonate; Neutralized1.4 Reagents: Triethylamine Solvents: Dichloromethane; 8 H,Rt
    标题:The Synthesis Of A Chiral β-Amino Acid Derivative By The Grignard Reaction Of An Aspartic Acid Equivalent
    作者:Liu,Feng; Et Al
    参考文献:Journal Of Chemical Research 日期:2010 卷标:34(9) 页码:517-519]

    1310689-94-1 + 327-52-6 = 881995-73-9
    反应条件:1.1 Reagents: Butylmagnesium Bromide Solvents: Tetrahydrofuran; -20 °C; 1 H,-20 °C1.2 Catalysts: N,N,N′,N′-Tetramethylethylenediamine,Cobalt Chloride (Cocl2) Solvents: Tetrahydrofuran; -20 °C; -15 °C -> -5 °C; -5 °C -> -20 °C; 0.5 H,0 °C; 30 Min,0 °C -> Rt1.3 Reagents: Hydrochloric Acid Solvents: Water
    标题:Synthesis Of A Chiral β-Amino Acid Derivative By A Cobalt-Catalysed Coupling Reaction
    作者:Pan,Xianhua; Et Al
    参考文献:Journal Of Chemical Research 日期:2011 卷标:35(9) 页码:545-546
📜Boc-L-天冬氨酸 4-甲酯置于咪唑,溴丁基-镁,Sodium Tetrahydroborate,溴,N,N'-二环己基碳二亚胺,三苯基膦体系中,用 四氢呋喃,甲醇,二氯甲烷,乙酸乙酯 作为反应溶剂,化学反应 2.75H,反应生成 (3R)-N-叔丁氧羰基-3-氨基-4-(2,4,5-三氟苯基)丁酸甲酯
参考文献:Synthesis Of A Chiral β-Amino Acid Derivative By A Cobalt-Catalysed Coupling Reaction
标题:Synthesis Of A Chiral β-Amino Acid Derivative By A Cobalt-Catalysed Coupling Reaction
摘要:通过钴催化 2,4,5-三氟苯基溴化镁与 L-天冬氨酸的烷基卤化物衍生物的烷基化反应,使用高效催化试剂合成了一种手性 β-氨基酸衍生物:Cocl2/tmeda.卤化物衍生物是由受保护的 L-天冬氨酸 β-甲基酯合成的,格氏试剂是通过溴镁交换制成的.l-天冬氨酸的立体结构保存完好.
DOI:10.3184/174751911X13155906432537

海关参考信息

专利信息


专利号:US-8471057-B2
优先权日:2009-09-27
标 题:Sitagliptin intermediates, preparation methods and uses thereof
发明人：ZHU GUOLIANG; ZHANG JIAN; YANG LIJUN; YAO QINGDAN; YING JIE
权利人:ZHU GUOLIANG; ZHANG JIAN; YANG LIJUN; YAO QINGDAN; YING JIE; ZHEJIANG JIUZHOU PHARM CO LTD
摘要:The present invention relates to Sitagliptin intermediate and preparation method and use thereof. The method comprises reacting compound of formula (II) and trifluorobromobenzene with a Grignard reagent by a Grignard reaction to obtain a compound of formula (I). Compound of formula (I) is a new intermediate compound for the synthesis of Sitagliptin. Compound of formula (I) can be easily used for preparing another important intermediate compound of formula (V) for the synthesis of Sitagliptin. The structures of the compounds mentioned above are as the following:

专利号:CN-115819260-B
优先权日:2022-11-28
标 题:A kind of synthesis process of sitagliptin intermediate

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合成参考文献


摘要:Kleemann, A.; Engel, J.; Kutscher, B.; Reichert, D., Pharmaceutical Substances[Online], Thieme: Stuttgart, (2007).
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