CAS: 881995-70-6; (Z)-Methyl 3-Amino-4-(2,4,5-Trifluorophenyl)But-2-Enoate

英文名称(Z)-Methyl 3-Amino-4-(2,4,5-Trifluorophenyl)But-2-Enoate
中文名称西他列汀-int A3
IUPAC名称methyl (Z)-3-amino-4-(2,4,5-trifluorophenyl)but-2-enoate
其它别名(Z)-Methyl 3-Amino-4-(2,4,5-Trifluorophenyl)But-2-Enoate; 2-Butenoic Acid, 3-Amino-4-(2,4,5-Trifluorophenyl)-, Methyl Ester, (2Z)-; Sitagliptin Impurity 95; Methyl (2Z)-3-Amino-4-(2,4,5-Trifluorophenyl)-2-Butenoate; (Z)-Methyl 3-Amino-4-(2,4,5-Trifluorophenyl)But-2-Enoate? (Sitagliptin Impurity）; (Z)-Methyl3-Amino-4-(2,4,5-Trifluorophenyl)-2-Butenoate
CAS编号881995-70-6
MFCD编号:MFCD26961273
分子式:C11H10F3NO2分子量:245.2
产品CID: 1891294
产品分类分析化学 → 标准品 → 药典标准品和杂质标准品

相似结构搜索
InChIKey: XKJLQAJESSUVAA-DAXSKMNVSA-N
InChI=1S/C11H10F3NO2/c1-17-11(16)4-7(15)2-6-3-9(13)10(14)5-8(6)12/h3-5H,2,15H2,1H3/b7-4-
计算化学: 氢键受体数6.0氢键供体数1.0可旋转键数4.0

MSDS等安全信息

上下游产品

4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester (2,4,5-trifluorophenyl)acetic acid 5-(1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione methanol (R)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid methyl ester 3-(R)-tert-butoxycarbonylamino-4-(2,4,5-trifluorophenyl)butyric acid methyl ester (Z)-3-acetylamino-4-(2,4,5-trifluorophenyl)-2-butenoic acid methyl ester (Z)-3-tert-butoxycarbonylamino-4-(2,4,5-trifluorophenyl)-2-butenoic acid methyl ester

合成工艺路线路线简述

合成目标产物 (Z)-Methyl 3-Amino-4-(2,4,5-Trifluorophenyl)But-2-Enoate 主要起始原料 Methanol And 5-1-Hydroxy-2-(2,4,5-Trifluorophenyl)Ethylidene-2,2-Dimethyl-1,3-Dioxane-4,6-Dione
769195-26-8 = 881995-70-6
反应条件:1.1 Reagents: Ammonium Acetate Solvents: Methanol; 7 H,Reflux
标题:Synthesis,Biological Evaluation And Structural Determination Of β-Aminoacyl-Containing Cyclic Hydrazine Derivatives As Dipeptidyl Peptidase Iv (Dpp-Iv) Inhibitors
作者:Ahn,Jin Hee; Et Al
参考文献:Bioorganic & Medicinal Chemistry Letters 日期:2007 卷标:17(9) 页码:2622-2628]

209995-38-0 + 38330-80-2 = 881995-70-6
反应条件:1.1 Reagents: 1,1′-Carbonyldiimidazole Solvents: Acetonitrile; 0.5 H,Rt; 3 H; Rt1.2 Reagents: Triethylamine,Magnesium Chloride Solvents: Acetonitrile; Rt -> 50 °C; 8 H,50 °C; 50 °C -> 30 °C1.3 2 H,30 °C; 24 H,30 °C; 30 °C -> 0 °C1.4 Reagents: Hydrochloric Acid Solvents: Water; 2 H,0 °C2.1 Reagents: Ammonium Acetate Solvents: Methanol; 2 H,Reflux
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

📜3-氧代-4-(2,4,5-三氟苯基)丁酸甲酯置于乙酸铵体系中,用甲醇作为反应溶剂,化学反应 2.0H,以91%的收率获得产物西他列汀-Int A3
参考文献:Application Of The Asymmetric Hydrogenation Of Enamines To The Preparation Of A Beta-Amino Acid Pharmacophore
标题:Application Of The Asymmetric Hydrogenation Of Enamines To The Preparation Of A Beta-Amino Acid Pharmacophore
摘要:(3R)-3-[n-(叔丁氧基羰基)氨基]-4-(2,4,5-三氟苯基)丁酸7A是通过使用手性五氟配体i和ii以及[rh(Cod)Cl]₂对烯胺酯3进行不对称氢化而合成的.直接还原3得到氨基酯1B,Ee值为93%,随后将其分离为(S)-樟脑磺酸盐以将对映体过量提升至>99%.还开发了一种更简洁的方法,涉及使用双特丁基碳酸酯对1B进行原位保护.该方法通过氢化直接提供目标n-Boc氨基酯7B,Ee值为97%,在结晶后ee值提升至>99%.©2006 Elsevier Ltd.出版.
DOI:10.1016/j.Tetasy.2005.12.016