L-正缬氨酸叔丁酯盐酸盐 | 119483-47-5

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 缬氨酸类衍生物
• 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
• 中文名称: L-正缬氨酸叔丁酯盐酸盐
• 英文名称: (2S)-aminopentanoic acid tert-butyl ester hydrochloride
• 英文别名: tert-butyl (2S)-2-aminopentanoate hydrochloride；L-norvaline t-butyl ester hydrochloride；L-norvaline tert-butyl ester hydrochloride；H₂N-Nva-Ot-Bu hydrochloride；(2S) 2-amino-pentanoic acid tert-butyl ester hydrochloride；(S)-tert-butyl 2-aminopentanoate hydrochloride；(L)-NVAOTBU HCl；tert-butyl (2S)-2-aminopentanoate;hydrochloride
• CAS: 119483-47-5
• 化学式: C₉H₁₉NO₂*ClH
• mdl: MFCD00190972
• 分子量: 209.716
• InChiKey: YQHANSSYWITJHA-FJXQXJEOSA-N

物化性质

• 熔点：
  140-145°C

计算性质

• 辛醇/水分配系数(LogP)：
  1.59
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.888
• 拓扑面积：
  52.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险类别码：
  R52
• 海关编码：
  2922499990
• 安全说明：
  S22,S24/25
• 储存条件：
  存储温度应保持在0°C。

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: L-Norvaline tert-butyl ester, HCl
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H412: Harmful to aquatic life with long lasting effects
P273: Avoid release to the environment

---

Section 3. Composition/information on ingredients.
Ingredient name: L-Norvaline tert-butyl ester, HCl
CAS number: 119483-47-5

---

Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

---

Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

---

Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

---

Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Storage: Store in closed vessels.

---

Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

---

Section 9. Physical and chemical properties
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C9H19NO2.ClH
Molecular weight: 209.7

---

Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, hydrogen chloride.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  L-正缬氨酸叔丁酯盐酸盐 在 palladium on activated charcoal 氢气 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 (S)-2-(2-oxo-2,3-dihydro-benzimidazol-1-yl)-pentanoic acid tert-butyl ester
  参考文献：
  名称：

  WO2008/147697

  摘要：

  公开号：
• 作为产物：
  描述：

  (2S)-(N-para-toluenesulphonylamino)pentanoic acid tert-butyl ester 在 盐酸 、 硫酸 、 氢溴酸 、 溶剂黄146 、 苯酚 作用下， 反应 40.0h， 生成 L-正缬氨酸叔丁酯盐酸盐
  参考文献：
  名称：

  氨基酸的合成通过与有机金属试剂的N-磺酰氮丙啶-2-羧酸酯的开环。

  摘要：

  作为制备旋光氨基酸的方法，已经研究了旋光N-磺酰基氮丙啶-2-羧酸酯与有机金属试剂的亲核开环。

  DOI：

  10.1016/s0040-4020(01)87968-0

文献信息

• Macrocyclic Modulators of the Ghrelin Receptor
  申请人：Ocera Therapeutics, Inc.

  公开号：US20180110824A1

  公开（公告）日：2018-04-26

  The present invention provides novel conformationally-defined macrocyclic compounds that have been demonstrated to be selective modulators of the ghrelin receptor (growth hormone secretagogue receptor, GHS-R1a and subtypes, isoforms and variants thereof). Methods of synthesizing the novel compounds are also described herein. These compounds are useful as agonists of the ghrelin receptor and as medicaments for treatment and prevention of a range of medical conditions including, but not limited to, metabolic and/or endocrine disorders, gastrointestinal disorders, cardiovascular disorders, obesity and obesity-associated disorders, central nervous system disorders, genetic disorders, hyperproliferative disorders and inflammatory disorders.

  本发明提供了一种新颖的构象定义明确的大环化合物，已经证明是生长激素分泌素受体（GHS-R1a及其亚型、异构体和变体）的选择性调节剂。本文还描述了合成这些新型化合物的方法。这些化合物可用作生长激素分泌素受体的激动剂，用于治疗和预防一系列医疗状况，包括但不限于代谢和/或内分泌紊乱、胃肠道紊乱、心血管疾病、肥胖和与肥胖相关的疾病、中枢神经系统疾病、遗传疾病、过度增殖性疾病和炎症性疾病。
• Evaluation of transition-state mimics in a superior BACE1 cleavage sequence as peptide-mimetic BACE1 inhibitors
  作者：Yasunao Hattori、Kazuya Kobayashi、Ayaka Deguchi、Yukie Nohara、Tomomi Akiyama、Kenta Teruya、Akira Sanjoh、Atsushi Nakagawa、Eiki Yamashita、Kenichi Akaji

  DOI：10.1016/j.bmc.2015.07.023

  日期：2015.9

  A superior substrate sequence for BACE1 containing transition-state mimics at the scissile site was evaluated as a protease inhibitor. Hydroxymethylcarbonyl (HMC) and hydroxyethylamine (HEA) isosteres were selected as the transition state mimics, and incorporated into the scissile site of the superior sequence covering the P4 to P1’ sites (Glu-Ile-Thi-Thi*Nva; *denotes the cleavage site). Isosteres

  易位处含有过渡态模拟物的BACE1的优良底物序列被评估为蛋白酶抑制剂。选择羟甲基羰基（HMC）和羟乙胺（HEA）等位基因作为过渡态模拟物，并将其并入覆盖P 4至P 1 '位的上位序列的易剪位点（Glu-Ile-Thi-Thi * Nva；*表示卵裂位点）。分别合成具有不同的羟基绝对构型的等排体，并评价构型的效果。每个等排异构体的羟基构型均显示出对抑制活性的显着影响。反对-易位部位取代基的构型在HMC型抑制剂中具有有效的抑制活性，而HEA型抑制剂的抗构型则没有抑制活性。基于重组BACE1与每种抑制剂的复合物的X射线晶体学分析进行结构评估，可深入了解蛋白质-配体之间的相互作用，尤其是在主要位点。
• Chiral Arylated Amines via C−N Coupling of Chiral Amines with Aryl Bromides Promoted by Light
  作者：Geyang Song、Liu Yang、Jing‐Sheng Li、Wei‐Jun Tang、Wei Zhang、Rui Cao、Chao Wang、Jianliang Xiao、Dong Xue

  DOI：10.1002/anie.202108587

  日期：2021.9.20

  molecular Ni catalysis driven by light, which enables stereoretentive C-N coupling of optically active amines, amino alcohols, and amino acid esters with aryl bromides, with no need for any external photosensitizer. The method is effective for a wide variety of coupling partners, including those bearing functional groups sensitive to bases and nucleophiles, thus providing a viable alternative to accessing

  Buchwald-Hartwig CN 偶联反应已在有机合成中得到广泛应用。在过去二十年左右的时间里，已经引入了许多改进的催化剂，现在可以很容易地使用各种胺和芳基亲电试剂。然而，缺乏可用于偶联各种手性胺和芳基卤而不会侵蚀过量对映体 ( ee) 的方案）。本文报道了一种基于光驱动的分子 Ni 催化的方法，该方法能够使旋光胺、氨基醇和氨基酸酯与芳基溴进行立体保留 CN 偶联，无需任何外部光敏剂。该方法对多种偶联伙伴有效，包括那些带有对碱和亲核试剂敏感的官能团的偶联伙伴，从而为获取合成重要的手性N-芳基胺、氨基醇和氨基酸酯提供了可行的替代方案。92 个例子证明了它的可行性，ee高达 99% 。
• Synthesis of Sulfonimidamide-Based Amino Acid Building Blocks with Orthogonal Protecting Groups
  作者：Praveen K. Chinthakindi、Andrea Benediktsdottir、Ayah Ibrahim、Atta Wared、Carl-Johan Aurell、Anna Pettersen、Edouard Zamaratski、Per I. Arvidsson、Yantao Chen、Anja Sandström

  DOI：10.1002/ejoc.201801541

  日期：2019.2.7

  Sulfonimidamide‐based amino acid building blocks have been synthesized through one‐pot reductive chlorination from sulfonamides followed by nucleophilic substitution with amino acid esters under mild conditions. Suitable orthogonal protecting groups were investigated that also allowed easy separation of diastereomers and access to non‐chromophoric sulfonimidamides as well as cyclic acyl sulfonimidamides

  基于磺酰胺基酰胺的氨基酸结构单元是通过在磺胺酰胺中进行一锅还原氯化反应，然后在温和条件下用氨基酸酯进行亲核取代而合成的。研究了合适的正交保护基团，这些基团还可以轻松分离非对映异构体，并获得非发色的磺酰亚胺酰胺和环状酰基磺酰胺酰胺。
• HCV PROTEASE INHIBITORS AND USES THEREOF
  申请人：Green Brian E.

  公开号：US20100029686A1

  公开（公告）日：2010-02-04

  This invention relates to: (a) compounds of formula I and salts thereof that, inter alia, are useful as hepatitis C virus (HCV) inhibitors; (b) intermediates useful for the preparation of such compounds and salts; (c) pharmaceutical compositions comprising such compounds and salts; and (d) methods of use of such compounds, salts, and compositions.

  这项发明涉及：(a) 公式I的化合物及其盐，它们可用作丙型肝炎病毒（HCV）抑制剂；(b) 用于制备这种化合物和盐的中间体；(c) 包含这种化合物和盐的药物组合物；以及(d) 使用这种化合物、盐和组合物的方法。