N-(1-ethoxycarbonyl-3-phenylpropyl)-L-alanine | 877932-98-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(1-ethoxycarbonyl-3-phenylpropyl)-L-alanine
• 英文别名: N-[1-(S)-Ethoxycarbonyl-3-phenylpropyl]-(S)-alanine；(S,S)-N-(1-ethoxycarbonyl-3-phenylpropyl) alanine；N-(1-(S)-ethoxycarbonyl-3-phenylpropyl)-L-alanine；N-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine；(S)-N-[1-(ethoxycarbonyl)-3-phenylpropyl]alanine；(S,S)-N-(1-ethoxycarbonyl-3-phenylpropyl)alanine；(2S)-2-[(1-ethoxy-1-oxo-4-phenylbutan-2-yl)amino]propanoic acid
• CAS: 877932-98-4
• 化学式: C₁₅H₂₁NO₄
• 分子量: 279.336
• InChiKey: CEIWXEQZZZHLDM-AMGKYWFPSA-N

物化性质

• 沸点：
  441.2±45.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  cis-4-(4-fluorophenoxy)-L-proline, methyl ester, hydrochloride 、 N-(1-ethoxycarbonyl-3-phenylpropyl)-L-alanine 生成 (S,S)-1-[N-(1-ethoxycarbonyl-3-phenylpropyl)-L-alanyl]-4-(4-fluorophenoxy)-L-proline
  参考文献：
  名称：

  Carboxyalkyl amino acid derivatives of various substituted prolines

  摘要：

  公开了化学式为##STR1##的羧基烷基二肽，其中R.sub.4是3-、4-、5-或4,4-取代的脯氨酸。这些化合物由于其抑制血管紧张素转化酶活性而可用作降压药物。

  公开号：

  US04462943A1
• 作为产物：
  描述：

  2-氧代-4-苯基丁酸乙酯 在 palladium on activated charcoal 氢气 、 sodium acetate 、 sodium cyanoborohydride 作用下， 以 甲醇 、 乙醇 为溶剂， 25.0 ℃ 、405.3 kPa 条件下， 反应 20.0h， 生成 N-(1-ethoxycarbonyl-3-phenylpropyl)-L-alanine
  参考文献：
  名称：

  Nonpeptide renin inhibitors employing a novel 3-aza (or oxa)-2,4-dialkyl glutaric acid moiety as a P2/P3 amide bond replacement

  摘要：

  A new series of renin inhibitors has been developed. The inhibitors feature a novel replacement for the P2/P3 dipeptide moiety normally associated with renin inhibitors. The dipeptide replacement was a (2S,4S)-3-aza(or oxa)-2,4-di-alkylglutaric acid amide. Extensive structure-activity relationship studies determined that optimum potency was achieved when inhibitors employed a benzyl and butyl group at the C(4) and C(2) carbon position, respectively. In addition, maximum in vitro potency was obtained when the N-terminus was functionalized by incorporating a 4-(1,3-dioxabutyl)piperidine amide. SAR data suggested that the 1,3-dioxabutyl group (methoxymethyl ether) interacted by hydrogen bonding to groups in the S4 domain of renin. This hypothesis was strengthened when a 4-butylpiperidine amide was substituted and inhibitor potency decreased dramatically. Inhibitors employing this novel dipeptide mimic were prepared by coupling the glutaric acid amides with either the transition-state mimic (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane (18) or the hydroxyethylene dipeptide isostere. The glutaric acid amides were prepared by two general procedures. The first procedure involved the reductive amination of alpha-amino acid esters with alpha-keto esters. The second procedure involved the displacement reaction of alpha-bromo esters or acids with alpha-amino acid amides.

  DOI：

  10.1021/jm00088a006

文献信息

• PROCESS FOR PRODUCING AMINO ACID N-CARBOXYANHYDRIDE
  申请人：Fujita Yukihiro

  公开号：US20070015932A1

  公开（公告）日：2007-01-18

  The present invention provides a process for producing an amino acid N-carboxyanhydride, which comprises reacting an amino acid or a derivative thereof with a compound represented by the following formula (1): wherein R 1 and R 2 represent the same or different electron-withdrawing substituents and each independently are an optionally substituted acyl group, an optionally substituted alkyloxycarbonyl group, an optionally substituted perfluoroalkyl group, an optionally substituted perchloroalkyl group, a cyano group, a halogen atom, or a nitro group; and a and b are the same or different and each are an integer of 1-5.

  本发明提供了一种制备氨基酸N-羧酸酐的方法，该方法包括使氨基酸或其衍生物与以下式(1)表示的化合物反应： 其中，R1和R2表示相同或不同的吸电子取代基，各自独立地为可任选取代的酰基、可任选取代的烷氧羰基、可任选取代的全氟烷基、可任选取代的全氯烷基、氰基、卤素原子或硝基；且a和b相同或不同，各自为1至5的整数。
• [EN] PROCESS FOR THE PREPARATION OF AMIDES OF N-[1-(S)-(ETHOXYCARBONYL)-3-PHENYLPROPYL]-L-ALANINE<br/>[FR] PROCÉDÉ DE PRÉPARATION D'AMIDES DE N-[1-(S)-(ÉTHOXYCARBONYL)-3-PHÉNYLPROPYL]-L-ALANINE
  申请人：SANOFI AVENTIS DEUTSCHLAND

  公开号：WO2014202659A1

  公开（公告）日：2014-12-24

  A process for the production of amides of N-[1-(S)-(ethoxycarbonyl)-3-phenylpropyl]-L-alanine is described. The process can be used for the production of key intermediates and finally the ACE inhibitors such as Ramipril, Enalapril, Quinapril, Trandolapril, Delapril and Moexipril starting from N-[1-(S)-(ethoxycarbonyl)-3-phenylpropyl]-L-alanine by the reaction with the appropriate amines.

  描述了一种制备N-[1-(S)-(乙氧羰基)-3-苯基丙基]-L-丙氨酸酰胺的方法。该工艺可用于从N-[1-(S)-(乙氧羰基)-3-苯基丙基]-L-丙氨酸出发，通过与适当的胺类反应，生产关键中间体，最终生产ACE抑制剂，如雷米普利、依那普利、喹那普利、群多普利、地拉普利和莫昔普利。
• [EN] PROCESS FOR THE PREPARATION OF N-CARBOXYANHYDRIDES<br/>[FR] PROCEDE DE PREPARATION DE N-CARBOXYANHYDRIDES
  申请人：BIOCON LTD

  公开号：WO2006027788A1

  公开（公告）日：2006-03-16

  The invention relates to a process for the preparation of N-carboxyanhydrides by reaction of the corresponding amino acid with phosgene, diphosgene and/or triphosgene in a solvent medium, characterized in that the reaction is a least partially carried out in the presence of an unsaturated organic compound which has one or more ethylenic double bonds. The N-carboxyanhydrides are thus obtained with better yields and an improved purity.

  本发明涉及一种通过相应的氨基酸与光气、偶氮光气和对光气在溶剂介质中反应来制备N-甲酰基酐的方法，其特征在于反应至少部分地在具有一个或多个乙烯双键的不饱和有机化合物存在下进行。因此，获得的N-甲酰基酐具有更好的收率和提高了纯度。
• [EN] NOVEL METHOD FOR PREPARATION OF CRYSTALLINE PERINDOPRIL ERBUMINE<br/>[FR] NOUVELLE METHODE DE PREPARATION DE PERINDOPRIL ERBUMINE CRISTALLINE
  申请人：LUPIN LTD

  公开号：WO2005037788A1

  公开（公告）日：2005-04-28

  A process for preparation of crystalline perindopril erbumine of formula (II) which exhibits the X-ray (powder) diffraction pattern like that shown in the figure. The process comprises reacting a solution of perindopril of formula (I), in a solvent selected from N, N-dimethylformamide or dimethyl acetals of lower aliphatic aldehydes and ketones with tertiary butylamine and crystallization of the erbumine salt thus obtained by heating the reaction mixture to reflux, filtering hot, cooling gradually to 20 ºC to 30 ºC, and further cooling to 0º C to 15 ºC for 30 minutes to 1 hour and finally filtering off and drying the crystals.

  一种制备结晶盐酸培哌普利的方法，其化学式为(II)，表现出X射线（粉末）衍射图谱，类似于所示图中的图谱。该方法包括将化学式(I)的培哌普利溶液在从N,N-二甲基甲酰胺或低碳链脂肪醛和酮的二甲基缩醛中选择的溶剂中与叔丁胺反应，并通过加热反应混合物至沸腾，热过滤，逐渐冷却至20°C至30°C，进一步冷却至0°C至15°C 30分钟至1小时，最后过滤和干燥晶体来结晶盐酸培哌普利。
• Process for preparing carboxyalkyl dipeptides
  申请人：Torcan Chemical Ltd.

  公开号：US04808741A1

  公开（公告）日：1989-02-28

  Pharmaceutically active carboxyalkyl dipeptides such as enalapril, lisinopril and the like, are prepared from a starting amino acid such as L-alanine, by protecting the acid function of the amino acid with an alkyl silyl protecting group, while it is reacted with an .alpha.-halo ester, at its amino function. Subsequently, the silyl protectant is removed, and the acid group is reacted with the amino function of an appropriate amino acid such as L-proline, to form the dipeptide product.

  药用活性的羧基烷基二肽，如依那普利、利尿普利等，是从起始氨基酸如L-丙氨酸制备而成的，方法是用烷基硅烷保护基保护氨基酸的酸功能，同时与α-卤酸酯在其氨基功能上发生反应。随后，去除硅烷保护基，并将酸基与适当的氨基酸如L-脯氨酸的氨基功能发生反应，形成二肽产物。