CAS: 82717-96-2; (S)-2-(((S)-1-Ethoxy-1-Oxo-4-Phenylbutan-2-yl)Amino)Propanoic Acid

该化合物是一种氨酸衍生物,其独特结构包括一个乙氧碳基化合物组和一个苯丙基丙基侧链,其特点是氨酸衍生物具有独特的结构,该化合物通常被归类为一种非蛋白性氨基氨基酸,这意味着它不是在翻译过程中纳入蛋白的标准氨基酸之一,其分子结构表明它可能由于存在一级L-环氨基成分而表现出特定的立体化学特性.乙氧碳基化合物组可以影响其溶性和再活动,使其有可能在各种合成应用中发挥作用,包括丙酸合成合成和药用化学.此外,苯丙基丙基丙基苯基苯基会传播独特的生物活动或相互作用,这可能与药理学研究有关.

英文名称(S)-2-(((S)-1-Ethoxy-1-Oxo-4-Phenylbutan-2-yl)Amino)Propanoic Acid
中文名称N-[(S)-(+)-1-(乙氧羰基)-3-苯丙基]-L-丙氨酸
IUPAC名称((S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)-L-alanine
其它别名(S,S)-N-(1-Ethoxycarbonyl-3-phenylpropyl)alanine
CAS编号82717-96-2
MFCD编号:MFCD00209976
EINECS号:617-383-0
FDA UNII编号:10SZ4IJ77B
分子式:C15H21NO4
分子量:279.34
产品CID: 1817278
产品分类有机原料→生命科学→氨基酸及其衍生物→丙氨酸及其衍生物

相似结构搜索
InChIKey: CEIWXEQZZZHLDM-AAEUAGOBSA-N
InChI=1S/C15H21NO4/c1-3-20-15(19)13(16-11(2)14(17)18)10-9-12-7-5-4-6-8-12/h4-8,11,13,16H,3,9-10H2,1-2H3,(H,17,18)/t11-,13-/m0/s1…
计算化学: 氢键受体数4.0氢键供体数2.0可旋转键数8.0

相似化合物

90891-21-7 85196-26-5 82717-96-2

物理性质

熔点150-152°C
沸点441.2°C at 760 mmHg
闪点220.6±28.7 °C
密度1.1±0.1 g/cm3
PH:+28° (20°C/D)(c=1, CH3OH)
pKa:2.14±0.10(预测)
PSA:75.63
LogP:1.6136
折射率1.524
蒸汽压0.0±1.1 mmHg at 25°C
溶解性6G/l
外观形态白色结晶粉末
储存条件请置于阴暗处, 惰性气氛中,室温
产品应用依那普利中间体.
性质描述白色细结晶性粉末.熔点148-152°C,比旋度+26.5°-+29.0°.

MSDS等安全信息

GHS象形图
GHS符号GHS07;
注释: Exclamation mark
危险类别特定目标器官毒性 - 单次接触类别3
皮肤腐蚀/刺激类别2
严重眼刺激类别2
警示词Warning(警告)
危险描述H335 |可能引起呼吸道刺激.
H315 |造成皮肤刺激.
H319 |造成严重眼刺激.
防范说明P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501
UN编号NONH for all modes of transport
危险品标志Xi
安全声明37/39-26-36
危险类别码36/37/38
WGK Germany3

欧盟法规

C&L通报REACH预注册

上下游产品

合成工艺路线路线简述

合成目标产物 N-[(S)-(+)-1-(Ethoxycarbonyl)-3-Phenylpropyl]-L-Alanine 主要起始原料 Benzenebutanoic Acid, α-[[(1S)-1-Methyl-2-Oxo-2-(Phenylmethoxy)Ethyl]Amino]-γ-Oxo-, Ethyl Ester, (αs)-
82717-95-1 = 82717-96-2
反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol
标题:Studies On Angiotensin Converting Enzyme Inhibitors. 4. Synthesis And Angiotensin Converting Enzyme Inhibitory Activities Of 3-Acyl-1-Alkyl-2-Oxoimidazolidine-4-Carboxylic Acid Derivatives
作者:Hayashi,Kimiaki; Et Al
参考文献:Journal Of Medicinal Chemistry 日期:1989 卷标:32(2) 页码:289-97]

87269-98-5 = 82717-96-2
反应条件:1.1 Reagents: Hydrogen,Sulfuric Acid Catalysts: Palladium Solvents: Acetic Acid; 10 H,0.8 - 1 Mpa,18 - 40 °C; 2 H,18 - 40 °C
标题:Synthesis Of Enalapril Maleate
作者:Tong,Guotong
参考文献:Huagong Shikan 日期:2006 卷标:20(3) 页码:29-30]

87269-98-5 = 82717-96-2
反应条件:1.1 Reagents: Acetic Acid,Sulfuric Acid Catalysts: Palladium; 6 H,Rt1.2 Reagents: Potassium Acetate; 1 H,Rt; Overnight,Rt
标题:Asymmetric Synthesis Of Quinapril
作者:Sun,Ping-Hua; Et Al
参考文献:Zhongguo Xinyao Zazhi 日期:2006 卷标:15(22) 页码:1945-1947]

80828-38-2 = 82717-96-2
反应条件:1.1 Reagents: Trifluoroacetic Acid Solvents: Trifluoroacetic Acid
标题:A Practical And Diastereoselective Synthesis Of Angiotensin Converting Enzyme Inhibitors
作者:Iwasaki,Genji; Et Al
参考文献:Chemical & Pharmaceutical Bulletin 日期:1989 卷标:37(2) 页码:280-3]

80828-38-2 = 82717-96-2
反应条件:1.1 Reagents: Trifluoroacetic Acid
标题:A Stereoselective Synthesis Of N-[(S)-1-(Ethoxycarbonyl)-3-Phenylpropyl]-L-Alanine Derivatives By Means Of Reductive Amination
作者:Iwasaki,Genji; Et Al
参考文献:Chemistry Letters 日期:1988 卷标:(10) 页码:1691-4]

56-41-7 + 82586-61-6 = 82717-96-2
反应条件:1.1 Reagents: Potassium Carbonate Solvents: Water; Rt1.2 Solvents: Dimethylformamide; 0.5 - 1 H,0 °C1.3 Reagents: Hydrochloric Acid Solvents: Water; Ph 4 - 5
标题:New Process For Medicine Intermediate Ecppa
作者:Jia,Jian-Hong; Et Al
参考文献:Zhejiang Gongye Daxue Xuebao 日期:2006 卷标:34(5) 页码:509-512]

13404-22-3 + 121842-77-1 = 82717-96-2
反应条件:1.1 Reagents: Potassium Carbonate Solvents: Acetonitrile2.1 Reagents: Trifluoroacetic Acid Solvents: Trifluoroacetic Acid
标题:A Practical And Diastereoselective Synthesis Of Angiotensin Converting Enzyme Inhibitors
作者:Iwasaki,Genji; Et Al
参考文献:Chemical & Pharmaceutical Bulletin 日期:1989 卷标:37(2) 页码:280-3]

17450-56-5 + 17831-01-5 = 82717-96-2 [标题:Reaction Conditions
标题:Improved Method For The Total Synthesis Of Oral Angiotensin Converting Enzyme Inhibitor - "Enalapril"
作者:Qiao,Ying; Et Al
参考文献:Beijing Daxue Xuebao 日期:1988 卷标:24(4) 页码:419-24]

104-15-4 + 17450-56-5 + 17831-01-5 = 82717-96-2
反应条件:1.1 Reagents: Triethylamine Solvents: Ethanol; 32 H,15 °C2.1 Reagents: Hydrogen,Sulfuric Acid Catalysts: Palladium Solvents: Acetic Acid,Water; 72 H,1.4 Mpa,30 °C
标题:Synthesis Of Quinapril Hydrochloride
作者:Tang,Linsheng; Et Al
参考文献:Zhongguo Yiyao Gongye Zazhi 日期:2009 卷标:40(8) 页码:563-566]

17450-56-5 + 56-41-7 = 82717-96-2
反应条件:1.1 Reagents: Lithium Hydroxide Solvents: Ethanol,Water; 30 Min,Rt1.2 Solvents: Ethanol; 5 °C; 10 Min,5 °C1.3 Reagents: Hydrochloric Acid Solvents: Water; 2 H,Ph 4.5,5 °C2.1 Reagents: Hydrogen,Sulfuric Acid Catalysts: Palladium Solvents: Ethanol,Water; 8 H,0.3 - 0.4 Mpa,30 °C2.2 Reagents: Sodium Acetate; 1 H,Rt
标题:Synthesis Of N-((S)-1-Ethoxycarbonyl-3-Phenylpropyl)-L-Alanine
作者:Zhang,Lijie; Et Al
参考文献:Huagong Jishu Yu Kaifa 日期:2011 卷标:40(4) 页码:11-12]

56-41-7 + 64920-29-2 = 82717-96-2 + 84324-12-9
反应条件:1.1 Reagents: Sodium Cyanoborohydride Solvents: Ethanol,Acetic Acid
标题:Synthesis Of Tritium-Labeled Enalapril Maleate
作者:Bartroli,J.; Et Al
参考文献:Journal Of Labelled Compounds And Radiopharmaceuticals 日期:1986 卷标:23(7) 页码:771-6]

87269-98-5 = 82717-96-2
反应条件:1.1 Reagents: Hydrogen,Sulfuric Acid Catalysts: Palladium Solvents: Acetic Acid,Water; 72 H,1.4 Mpa,30 °C
标题:Synthesis Of Quinapril Hydrochloride
作者:Tang,Linsheng; Et Al
参考文献:Zhongguo Yiyao Gongye Zazhi 日期:2009 卷标:40(8) 页码:563-566]

80828-38-2 = 82717-96-2 [标题:Reaction Conditions
标题:N-Substituted Glycine Compounds
参考文献:Japan]

90988-18-4 = 82717-96-2 [标题:Reaction Conditions
标题:Substituted Acyl Derivatives Of Octahydro-1H-Isoindole-1-Carboxylic Acids And Esters
参考文献:European Patent Organization]

710-11-2 + 13404-22-3 + 1117-96-0 = 82717-96-2
反应条件:1.1 Reagents: Sodium Acetate Solvents: Dichloromethane1.2 Reagents: Catecholborane Solvents: Dichloromethane1.3 -2.1 Reagents: Trifluoroacetic Acid
标题:A Stereoselective Synthesis Of N-[(S)-1-(Ethoxycarbonyl)-3-Phenylpropyl]-L-Alanine Derivatives By Means Of Reductive Amination
作者:Iwasaki,Genji; Et Al
参考文献:Chemistry Letters 日期:1988 卷标:(10) 页码:1691-4]

17831-01-5 + 15121-89-8 = 82717-96-2
反应条件:1.1 Reagents: Triethylamine Solvents: Ethanol; Rt; 1 H,Rt; Overnight,Rt2.1 Reagents: Acetic Acid,Sulfuric Acid Catalysts: Palladium; 6 H,Rt2.2 Reagents: Potassium Acetate; 1 H,Rt; Overnight,Rt
标题:Asymmetric Synthesis Of Quinapril
作者:Sun,Ping-Hua; Et Al
参考文献:Zhongguo Xinyao Zazhi 日期:2006 卷标:15(22) 页码:1945-1947]

104-15-4 + 17450-56-5 + 17831-01-5 = 82717-96-2
反应条件:1.1 Reagents: Triethylamine Solvents: Ethanol; 1 H,40 °C; 40 °C -> 0 °C2.1 Reagents: Hydrogen,Sulfuric Acid Catalysts: Palladium Solvents: Acetic Acid; 10 H,0.8 - 1 Mpa,18 - 40 °C; 2 H,18 - 40 °C
标题:Synthesis Of Enalapril Maleate
作者:Tong,Guotong
参考文献:Huagong Shikan 日期:2006 卷标:20(3) 页码:29-30]

17831-01-5 + 82586-61-6 = 82717-96-2
反应条件:1.1 -2.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol
标题:Studies On Angiotensin Converting Enzyme Inhibitors. 4. Synthesis And Angiotensin Converting Enzyme Inhibitory Activities Of 3-Acyl-1-Alkyl-2-Oxoimidazolidine-4-Carboxylic Acid Derivatives
作者:Hayashi,Kimiaki; Et Al
参考文献:Journal Of Medicinal Chemistry 日期:1989 卷标:32(2) 页码:289-97]

1821-12-1 = 82717-96-2
反应条件:1.1 Reagents: Phosphorus Trichloride; 0.5 H,Reflux1.2 Reagents: Bromine; 3 - 4 H,< 70 °C; 70 °C -> 30 °C1.3 Reagents: Sulfuric Acid Solvents: Water1.4 Solvents: Ethanol; 3 H,60 °C2.1 Reagents: Potassium Carbonate Solvents: Water; Rt2.2 Solvents: Dimethylformamide; 0.5 - 1 H,0 °C2.3 Reagents: Hydrochloric Acid Solvents: Water; Ph 4 - 5
标题:New Process For Medicine Intermediate Ecppa
作者:Jia,Jian-Hong; Et Al
参考文献:Zhejiang Gongye Daxue Xuebao 日期:2006 卷标:34(5) 页码:509-512]

21691-50-9 + 64920-29-2 = 82717-96-2 [标题:Reaction Conditions
标题:N-Substituted Glycine Compounds
参考文献:Japan

群多普利反应 17.0H,反应生成 N-[1-(S)-乙氧羰基-3-苯丙基]-L-丙氨酸
参考文献:Impurity Profiling Of Trandolapril Under Stress Testing: Structure Elucidation Of By-Products And Development Of Degradation Pathway
标题:Impurity Profiling Of Trandolapril Under Stress Testing: Structure Elucidation Of By-Products And Development Of Degradation Pathway
摘要:Various Regulatory Authorities Like International Conference On Harmonization (Ich),Us Food And Drug Administration,Canadian Drug And Health Agency Are Emphasizing On The Purity Requirements And The Identification Of Impurities In Active Pharmaceutical Drugs. Qualification Of The Impurities Is The Process Of Acquiring And Evaluating Data That Establishes Biological Safety Of An Individual Impurity; Thus,Revealing The Need And Scope Of Impurity Profiling Of Drugs In Pharmaceutical Research.As No Stability-Indicating Method Is Available For Identification Of Degradation Products Of Trandolapril,A New Angiotensin Converting Enzyme Inhibitor (Ace!),Under Stress Testing,The Development Of An Accurate Method Is Needed For Quantification And Qualification Of Degradation Products. Ultra High Performance Liquid Chromatography (Uplc) Coupled To Electrospray Tandem Mass Spectrometry Was Used For The Rapid And Simultaneous Analysis Of Trandolapril And Its Degradation Products. Chromatographic Separation Was Achieved In Less Than 4 Min,With Improved Peak Resolution And Sensitivity. Thanks To This Method,The Kinetics Of Trandolapril Degradation Under Various Operating Conditions And The Characterization Of The Structure Of The By-Products Formed During Stress Testing Have Been Determined. Thereafter,A Mechanism Of Trandolapril Degradation In Acid And Neutral Conditions,Including All The Identified Products,Was Then Proposed. (C) 2012 Elsevier B.V. All Rights Reserved.
DOI:10.1016/j.Ijpharm.2012.08.048

海关参考信息

2902600000-乙苯
2905121000-正丙醇
2905130000-正丁醇
2909110000-乙醚
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详情请参考：📖 海关编码查询和海关进出口税则

专利信息

专利号:US-7973173-B2
优先权日:2005-07-05
标题:Process for the synthesis of an ACE inhibitor
发明人：KANKAN RAJENDRA NARAYANRAO; RAO DHARMARAJ RAMACHANDRA; PHULL MANJINDER SINGH; SAWANT ASHWINI; BIRARI DILIP RAMDAS
权利人:CIPLA LTD
摘要:A process for the synthesis of trandolapril which comprises condensing Nâ€”[Iâ€”(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine N-carboxyanhydride with trans octahydro-1H-indole-2-carboxylic acid in a first organic solvent comprising a water immiscible inert organic solvent and in the presence of a base, and isolating trandolapril from a second organic solvent. N-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine N-carboxyanhydride may also be condensed with (2S,3aR,7aS) octahydro-1H-indole-2-carboxylic acid in a first organic solvent and in the presence of a base, and trandolapril isolated. There is also provided a process for the resolution of racemic trans octahydro-1H-indole-2-carboxylc acid.

专利号:US-8263784-B2
优先权日:2008-10-30
标题 :Method for the synthesis of a ramipril intermediate
发明人：DE LANGE BEN; HEEMSKERK DENNIS
权利人:DE LANGE BEN; HEEMSKERK DENNIS; DSM SINOCHEM PHARM NL BV
摘要:The present invention relates to a process for the preparation of octahydrocyclopenta[b]pyrrole-2-carboxylic acid and esters thereof of general formula (1) in the presence of a cobalt and/or nickel comprising catalyst and to the use of compounds of general formula (1) in the synthesis of ramipril.

专利号:US-2007225505-A1
优先权日:2003-11-25
标题 :Method for the Preparation of (2S, 3AR, 7AS)-Octahydro-III-Indole-2-Carboxylic Acid as Key Intermediate in the Preparation of Trandolapril by Reacting a Cyclohexyl Aziridine with a Dialkyl Malonate
发明人：CID PAU
权利人:CID PAU
摘要:A method for the synthesis of a compound of formula I as a mixture of enantiomers, n n n(wherein R 1 is H or an acid protective group and H + A âˆ’ indicates an optional acid with which the compound of formula I may form an ammonium salt) nsaid method comprising; A) reacting a cyclohexyl aziridine with a dialkyl malonate, whereby to provide a trans-fused 3-alkylcarbonyl-octahydro-indol-2-one; B) decarbonylation at the 3-position, conversion of the ketone of the resulting trans-octahydro-indol-2-one to an optionally protected carboxylic acid group; and C) optionally removing any N-substitution if necessary.

专利号:WO-9633984-A1
优先权日:1995-04-24
标题:N-sulfoxy anhydrides, a process for the preparation thereof and its use for the preparation of bioactive substances having ace inhibitory action
发明人：SERRA MORTES SONIA; PALOMO COLL ALBERTO; ZUPET ROK
权利人:GENESIS PARA LA INVESTIGACION; SERRA MORTES SONIA; PALOMO COLL ALBERTO; ZUPET ROK
摘要:Novel N-sulfoxy anhydrides, a process for the preparation thereof and its use for the preparation of bioactive substances having ACE inhibitory action. Novel compounds of formula (III), wherein R1 represents PhCH2-CH2- or CH3CH2-CH2- and R2 represents methyl or R3-NH-(CH2)3-CH2-, wherein R3 has the meaning of amino protective group, are disclosed. They are used as intermediates in the synthesis of ACE inhibitors, especially of enalapril and trandolapril.

专利号:US-8288565-B2
优先权日:2009-07-16
标题 :Process for the synthesis of (2S,3AR,7AS)-octahydro-1H-indole carboxylic acid as an intermediate for trandolapril
发明人：CHEMBURKAR SANJAY R; REDDY RAJARATHNAM E; REAMER DOUGLAS M; PAVLINA JOHN T; ULREY STEPHEN S; KOTECKI BRIAN J
权利人:CHEMBURKAR SANJAY R; REDDY RAJARATHNAM E; REAMER DOUGLAS M; PAVLINA JOHN T; ULREY STEPHEN S; KOTECKI BRIAN J; ABBOTT LAB
摘要:A process for the preparation of (2S,3aR,7aS)-octahydro-1H-indole-20carboxylic acid hydrochloride.

专利号:US-6395918-B1
优先权日:1998-04-27
标题 :Conversion of a hydroxy group in certain alcohols into a fluorosulfonate ester or a trifluoromethylsulfonate ester
发明人：LOEWENTHAL HANS JACOB EDGAR; LOEWENTHAL RON BENJAMIN
摘要:The present invention provides a method of converting a hydroxy group in alcohols containing an electron withdrawing group into perfluoroalkane sulfonate and fluorosulfonate esters, which are good leaving groups, with inversion of configuration where the hydroxyl-bearing carbon is chiral. The method consists of converting an alcohol to an Oâ€”N,N-dialkylsulfamate ester and reacting it with a perfluoroalkansulfonic or fluorosulfonic acid. The method has applications in the synthesis of pharmaceutical and agrochemical compounds.

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企业联系电话：18267553885👤
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主要参考文献

[参考文献]: Luckose F, Et Al. Effects Of Amino Acid Derivatives On Physical, Mental, And Physiological Activities. Crit Rev Food Sci Nutr. 2015;55(13):1793-1101.

合成参考文献

摘要:Kleemann, A.; Engel, J.; Kutscher, B.; Reichert, D., Pharmaceutical Substances[Online], Thieme: Stuttgart, (2003).
摘要:Kleemann, A.; Engel, J.; Kutscher, B.; Reichert, D., Pharmaceutical Substances[Online], Thieme: Stuttgart, (2003).
摘要:Kleemann, A.; Engel, J.; Kutscher, B.; Reichert, D., Pharmaceutical Substances[Online], Thieme: Stuttgart, (2003).
摘要:Kleemann, A.; Engel, J.; Kutscher, B.; Reichert, D., Pharmaceutical Substances[Online], Thieme: Stuttgart, (2003).
摘要:Kleemann, A.; Engel, J.; Kutscher, B.; Reichert, D., Pharmaceutical Substances[Online], Thieme: Stuttgart, (2003).

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CAS: 82717-96-2; (S)-2-(((S)-1-Ethoxy-1-Oxo-4-Phenylbutan-2-yl)Amino)Propanoic Acid

相似化合物

物理性质

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