(R)-N-carboxybenzyloxy phenylglycinamide | 61342-58-3

• 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: (R)-N-carboxybenzyloxy phenylglycinamide
• 英文别名: benzyl [(1R)-2-amino-2-oxo-1-phenylethyl]carbamate；benzyl (R)-(2-amino-2-oxo-1-phenylethyl)carbamate；Cbz-D-Phg-NH2；N-(Benzyloxycarbonyl)-D-phenylglycinamid；H-D-Phg-NH2；benzyl N-[(1R)-2-amino-2-oxo-1-phenylethyl]carbamate
• CAS: 61342-58-3
• 化学式: C₁₆H₁₆N₂O₃
• 分子量: 284.315
• InChiKey: NTKPNKLUBASDQB-CQSZACIVSA-N

物化性质

• 沸点：
  520.7±50.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

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：

  (R)-N-carboxybenzyloxy phenylglycinamide 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以0.1 g的产率得到左旋苯甘氨酸酰胺
  参考文献：
  名称：

  [EN] COMPLEMENT MODULATORS AND RELATED METHODS
  [FR] MODULATEURS DU COMPLÉMENT ET PROCÉDÉS ASSOCIÉS

  摘要：

  本公开涉及与补体成分相互作用的化合物和组合物。一些化合物抑制补体活性。包括作为C5抑制剂化合物的小分子化合物和组合物。提供了抑制补体活性的方法以及利用C5抑制剂化合物和组合物治疗与补体相关症状的方法。

  公开号：

  WO2020205501A1
• 作为产物：
  描述：

  左旋苯甘氨酸 在 N,N'-羰基二咪唑 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 (R)-N-carboxybenzyloxy phenylglycinamide
  参考文献：
  名称：

  Retention of stereochemistry in the microwave assisted synthesis of 1H-tetrazole bioisosteric moiety from chiral phenyl-acetic acid derivatives

  摘要：

  Chiral substituted phenylethyl-1H-tetrazoles were built-up from the corresponding carboxylic acid derivatives by a useful three-step synthesis. The procedure, that preserves the chiral center from racemization, was successfully applied to a selection of several hit compounds by conversion of the carboxylic acid moiety to the nitrile derivatives and subsequent reaction with trimethylstannyl azide, under microwave conditions. A useful application to the corresponding tetrazole analogue has been found also in the conversion of the aminoacidic moiety like (R)-N-Cbz-phenylglycine showing a wide potential synthetic application. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.022

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）。
• Green diastereospecific synthesis of various medicine analogues containing dipeptides and release of the medicines by Baker's yeast
  作者：Sunghee Jung、Shin Satoh、Hideyuki Daitoku、Takuya Noguchi、Yuya Kawashima、Nobuyuki Imai

  DOI：10.1016/j.tet.2022.133102

  日期：2022.11

  dipeptides in 76–99% yields with 70–>99% de and dipeptides-containing medicine analogues in 74–99% yields with 79–97% de in aqueous THF at −15 °C via the mixed carbonic carboxylic anhydrides by the activation of the corresponding carboxylic acids. We observed that the anilide l-Phe-l-Phe-NHC6H4-4-OH, one of the deprotecting medicine analogues, was cleaved at the C-terminal of l-phenylalanine (l-Phe) by

  我们已经成功地以 76–99% 的收率和 70–>99% 的去氧化酶绿色和经济地合成了各种二肽和含二肽的药物类似物，在 -15 °C 的水性 THF 中以 79–97% 的去氧化酶的收率在 -15 °C 下通过通过相应羧酸的活化得到混合碳酸酐。我们观察到苯胺l -Phe- l -Phe-NHC 6 H 4 -4-OH 是一种脱保护药物类似物，在饥饿条件下被贝克酵母在l-苯丙氨酸 ( l -Phe) 的C端裂解条件，然后处理新鲜制备的 PhCH 2 CH 2 CO 2 CO 2Et 从 3-苯基丙酸、ClCO 2 Et 和 Et 3 N 在 MeCN 中得到 PhCH 2 CH 2 CONHC 6 H 4 -4-OH 和 PhCH 2 CH 2 CO - 1 -Phe-NHC 6 H 4 -4-OH收益率分别为 46% 和 42%。有趣的是，贝克酵母对l -Phe- d -Phe-NHC 6
• BENZAMIDES AND NICOTINAMIDES AS SYK MODULATORS
  申请人：Portola Pharmaceuticals, Inc.

  公开号：EP3176154A1

  公开（公告）日：2017-06-07

  The present invention is directed to compounds of formula I and pharmaceutically acceptable salts, esters, and prodrugs thereof which are inhibitors of Syk kinase. The present invention is also directed to intermediates used in making such compounds, the preparation of such a compound, pharmaceutical compositions containing such a compound, methods of inhibition Syk kinase activity, methods of inhibition the platelet aggregation, and methods to prevent or treat a number of conditions mediated at least in part by Syk kinase activity, such as Non Hodgkin's Lymphoma.

  本发明涉及式I化合物及其药学上可接受的盐、酯和原药，它们是Syk激酶的抑制剂。本发明还涉及用于制造此类化合物的中间体、此类化合物的制备方法、含有此类化合物的药物组合物、抑制 Syk 激酶活性的方法、抑制血小板聚集的方法，以及预防或治疗至少部分由 Syk 激酶活性介导的多种疾病（如非霍奇金淋巴瘤）的方法。