(S)-N-carboxybenzyloxy phenylglycinamide | 67861-68-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-N-carboxybenzyloxy phenylglycinamide
• 英文别名: benzyl [(1S)-2-amino-2-oxo-1-phenylethyl]carbamate；Cbz-L-Phg-NH2；Z-L-Phenylglycinamid；Z-L-Phg-NH2；benzyl N-[(1S)-2-amino-2-oxo-1-phenylethyl]carbamate
• CAS: 67861-68-1
• 化学式: C₁₆H₁₆N₂O₃
• 分子量: 284.315
• InChiKey: NTKPNKLUBASDQB-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-N-carboxybenzyloxy phenylglycinamide 在 lithium aluminium tetrahydride 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 20.0h， 生成 tert-butyl [(2S)-2-{[(3,4-dichlorophenyl)acetyl](methyl)amino}-2-phenylethyl]carbamate
  参考文献：
  名称：

  [EN] KAPPA OPIOID AGONISTS AND USES THEREOF
  [FR] AGONISTES OPIOÏDES KAPPA ET LEURS UTILISATIONS

  摘要：

  公开号：

  WO2014210436A3
• 作为产物：
  描述：

  (S)-(S)-2-(((benzyloxy)carbonyl)amino)-2-phenylacetic (ethyl carbonic) anhydride 在 氯化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 生成 (S)-N-carboxybenzyloxy phenylglycinamide
  参考文献：
  名称：

  方便的N-保护的苯基甘氨酸和二肽的初级酰胺化反应，而没有外消旋或差向异构

  摘要：

  N-保护的苯基甘氨酸和二肽的初次酰胺化反应容易进行，以57-95％的收率分别提供了99％ee和81-99％de的相应酰胺。通过在羧酸活化时将反应温度精确地保持在-15°C，然后使混合的碳羧酸酐与NH 4 Cl反应，该过程很容易避免反应中产物的外消旋和差向异构化。

  DOI：

  10.1016/j.tetlet.2013.11.042

文献信息

• Dehydration of Chiral α-Amides to Chiral α-Nitriles Under the Appel Reaction Conditions
  作者：Shekharappa、L. Roopesh Kumar、C. Srinivasulu、Vommina V. Sureshbabu

  DOI：10.1007/s10989-020-10101-y

  日期：2021.3

  Nα-protected amino acid amides to corresponding nitriles with neither harsh condition nor catalyst. Graphic Abstract Nα-protected amino acid amides were efficiently transformed to Nα-protected amino acid nitriles employing I2, PPh3, and NMM under mild reaction conditions. Fmoc, Boc and Cbz-protected amino acid amides were converted into their corresponding nitriles groups. Side chain protected amino acid amides

  N的有效的合成α -保护的氨基腈选自N α -保护的使用pH值氨基酰胺3 P，I 2和NMM被描述。受Fmoc，Z和Boc保护的各种氨基酸酰胺可方便地以高收率转化为腈。侧链保护的氨基酸酰胺具有良好的耐受性，并获得了良好的产物收率。该协议用作温和的一个，对于N的自由外消旋转换几个可用的，方法中α -保护的氨基酸酰胺与既不苛刻的条件，也没有催化剂相应的腈。 图形摘要 Ñ α -保护的氨基酸酰胺被有效转化成N α采用我-保护氨基酸腈2，PPH 3，和NMM温和的反应条件下进行。Fmoc，Boc和Cbz保护的氨基酸酰胺被转化为相应的腈基。侧链保护的氨基酸酰胺也容易以良好的产率转化为其相应的腈。
• Convenient primary amidation of N-protected phenylglycine and dipeptides without racemization or epimerization
  作者：Takuya Noguchi、Seunghee Jung、Nobuyuki Imai

  DOI：10.1016/j.tetlet.2013.11.042

  日期：2014.1

  Primary amidation of N-protected phenylglycine and dipeptide proceeded easily to afford the corresponding amides in 57–95% yields with 99% ee and 81–99% de, respectively. The procedure is very easy to avoid racemization and epimerization of the products in the reactions by keeping exactly the reaction temperature at −15 °C when the activation of carboxylic acids, followed by the reaction of the mixed

  N-保护的苯基甘氨酸和二肽的初次酰胺化反应容易进行，以57-95％的收率分别提供了99％ee和81-99％de的相应酰胺。通过在羧酸活化时将反应温度精确地保持在-15°C，然后使混合的碳羧酸酐与NH 4 Cl反应，该过程很容易避免反应中产物的外消旋和差向异构化。
• Phenylglycine-containing new peptides with gastrine effects and a
  申请人：Richter Gedeon Vegyeszeti Gyar Rt.

  公开号：US04183909A1

  公开（公告）日：1980-01-15

  The invention relates to novel peptides of formula (I), A-Try-B-Asp-Phg-NH.sub. 2 (I) wherein A is tert.-butoxycarbonyl-aminooxy-acyl, benzyloxycarbonyl-aminooxy-acyl, (aminooxy)-acyl or E-aminooxy-acyl, wherein E is benzoyl or straight-chained or branched C.sub.1-5 aliphatic acyl, and B represents methionyl, leucyl, norleucyl, norvalyl or 2-amino-decanoyl, or acid addition salts or complexes thereof. The novel compounds according to the invention exert gastrin effects and can be applied to advantage in the diagnostics and therapy. The novel compounds of formula (I) are prepared according to the invention by reacting a tetrapeptideamide of formula (II), H-Try-B-Asp-Phg-NH.sub. 2 (II) wherein B is as defined above, with an (aminooxy)-acyl containing compound of the general formula A.sub.1 -X, wherein A.sub.1 has the same meanings as A with the exception of the (aminooxy)-acyl, and X is hydroxy group, halogen, pivaloyloxy, a group of the formula R--O--CO.sub.2 -- (wherein R is lower alkyl, phenoxy which can have a nitro substituent or one or more halogen or N-succinimidoxy.

  本发明涉及公式（I）的新肽，A-Try-B-Asp-Phg-NH.sub.2（I），其中A是tert.-butoxycarbonyl-aminooxy-acyl，benzyloxycarbonyl-aminooxy-acyl，（aminooxy）-acyl或E-aminooxy-acyl，其中E是苯甲酰基或直链或支链C.sub.1-5脂肪酰基，B代表甲硫氨酰基，亮氨酰基，诺亮氨酰基，诺缩氨酰基或2-氨基癸酰基，或其酸加成盐或络合物。本发明的新化合物具有胃泌素效应，并可优势地应用于诊断和治疗。公式（I）的新化合物是通过将公式（II）的四肽酰胺，H-Try-B-Asp-Phg-NH.sub.2（II），其中B如上所定义，与含有（aminooxy）-acyl的化合物A.sub.1-X反应而制备的，其中A.sub.1除了（aminooxy）-acyl外具有与A相同的含义，X是羟基，卤素，皮瓦酰氧基，公式R-O-CO.sub.2-（其中R是低碳基，苯氧基可以有一个硝基取代基或一个或多个卤素或N-琥珀酰氧基）。
• KAPPA OPIOID AGONISTS AND USES THEREOF
  申请人：NEKTAR THERAPEUTICS

  公开号：US20160145245A1

  公开（公告）日：2016-05-26

  Provided are compounds of Formula I; and pharmaceutically acceptable salts and solvates thereof. The compounds of Formula I described herein relate to and/or have application(s) in (among others) the fields of drug discovery, pharmacotherapy, physiology, organic chemistry and polymer chemistry.

  提供的是公式I的化合物；以及其药学上可接受的盐和溶剂化合物。本文所描述的公式I的化合物与/或适用于（其中之一）药物发现、药理学、生理学、有机化学和高分子化学等领域。
• <i>N</i>-Urethane-Protected Amino Alkyl Isothiocyanates: Synthesis, Isolation, Characterization, and Application to the Synthesis of Thioureidopeptides
  作者：Vommina V. Sureshbabu、Shankar A. Naik、H. P. Hemantha、N. Narendra、Ushati Das、Tayur N. Guru Row

  DOI：10.1021/jo900675s

  日期：2009.8.7

  Synthetically useful N-Fmoc amino-alkyl isothiocyanates have been described, starting from protected amino acids. These compounds have been synthesized in excellent yields by thiocarbonylation of the monoprotected 1,2-diamines with CS2/TEA/p-TsCl, isolated as stable solids, and completely characterized. The procedure has been extended to the synthesis of amino alkyl isothiocyanates from Boc- and Z-protected amino acids as well. The utility of these isothiocyanates for peptidomimetics synthesis has been demonstrated by employing them in the preparation of a series of dithioureidopeptide esters. Boc-Gly-OH and Boc-Phe-OH derived isothiocyanates 9a and 9c have been obtained as single crystals and their structures solved through X-ray diffraction. They belong to the orthorhombic crystal system, and have a single molecule in the asymmetric unit (Z' = 1). 9a crystallizes in the centrosymmetric space group Pbca, while 9c crystallizes in the noncentrosymmetric space group P2(1)2(1)2(1).