N-[叔丁氧羰基]-L-色氨酸甲酯 | 33900-28-6

• 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: N-[叔丁氧羰基]-L-色氨酸甲酯
• 中文别名: BOC-L-色氨酸甲酯
• 英文名称: methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoate
• 英文别名: Boc-Trp-OMe；N-Boc-L-tryptophan methyl ester；(S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)propanoate；methyl (tert-butoxycarbonyl)-L-tryptophanate；Boc-L-Trp-OMe；methyl N-(tert-butoxycarbonyl)-L-tryptophanate；Boc-L-tryptophan methyl ester；N-Boc-tryptophan methyl ester；(L)-Boc-Trp-OMe；N-Boc-Trp-OMe；N-(tert-butoxycarbonyl)-L-tryptophan methyl ester；methyl (2S)-3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 33900-28-6
• 化学式: C₁₇H₂₂N₂O₄
• 分子量: 318.373
• InChiKey: QXLOVPXUZAOKBL-AWEZNQCLSA-N

物化性质

• 熔点：
  139-140 °C(Solv: ligroine (8032-32-4); ethyl acetate (141-78-6))
• 沸点：
  505.7±45.0 °C(Predicted)
• 密度：
  1.194±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  | 2-8°C |

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Boc-Trp-OMe
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: Boc-Trp-OMe
CAS number: 33900-28-6

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
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.

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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.

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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.

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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.
Store in closed vessels, refrigerated.
Storage:

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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.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C17H22N2O4
Molecular weight: 318.4

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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.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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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.

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

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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.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  N-[叔丁氧羰基]-L-色氨酸甲酯 在 盐酸 、 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 水 、 重水 、 silica gel 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲基叔丁基醚 为溶剂， 反应 38.0h， 生成 L-色氨酸
  参考文献：
  名称：

  顺序Ir催化反应合成2-D- L-色氨酸

  摘要：

  在本文中，我们报道了2-D-的实用合成升色氨酸通过顺序铱催化的Ç ħ硼化和Ir催化的C-2-deborylative氘化步骤。在该合成序列中，由于氘被氢取代，Boc和甲酯基团的脱保护被证明具有挑战性。然而，开发了温和的脱保护条件以避免这种D / H加扰。此外，2-D-大号-色氨酸在用于生物学研究的许多缓冲剂稳定。

  DOI：

  10.1016/j.tet.2019.02.054
• 作为产物：
  描述：

  L-色氨酸 在 溶剂黄146 作用下， 以 乙醚 、 水 为溶剂， 反应 2.0h， 生成 N-[叔丁氧羰基]-L-色氨酸甲酯
  参考文献：
  名称：

  水会抑制氨基酸的消旋化和分解吗？

  摘要：

  几个中性免费 氨基酸， 苯甘氨酸， 亮氨酸， 苯丙氨酸 和 色氨酸在碱性或酸性条件下在100–130°C下加热 水 或各种极性有机物 溶剂。尽管严重的消旋和分解 发生在极性有机物中 溶剂 例如DMF， 二甲基亚砜， 或者 乙二醇在碱性条件下（K 2 CO 3，酸值（Et 3 N），这些现象不会发生或在很大程度上减少水 或含水有机 溶剂在相同的碱性条件下。严重的消旋和分解 免费 苯甘氨酸 在AcOH中也观察到 水 或含水AcOH（<90％）在很大程度上抑制了消旋作用， 分解。我们讨论了这种抑制作用的可能原因。水 就碱的解溶剂和解离状态而言 氨基酸 在水性和有机状态 溶剂。

  DOI：

  10.1039/b102254g
• 作为试剂：
  描述：

  D-薄荷醇 在 2,6-二甲基吡啶 、 硫酸 、 bis[3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridyl]phenyl]iridium(1+); 2-(2-pyridyl)pyridine; hexafluorophosphate 、 N-[叔丁氧羰基]-L-色氨酸甲酯 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 29.0h， 生成
  参考文献：
  名称：

  通过吲哚 (C-2) 光催化烷基化对色氨酸保护的肽序列进行后合成功能化

  摘要：

  我们报告了在可见光照射下用活化的 α-溴-羰基化合物对色氨酸和含色氨酸的肽进行选择性、温和和有效的 C-H 功能化。该协议的效率由广泛的底物范围和氨基酸侧链中存在的敏感官能团的出色耐受性概述。该方法可以成功扩展到访问药物肽缀合物支架。

  DOI：

  10.1039/d1cc01822a

文献信息

• Copper‐Promoted N‐Arylation of the Indole Side Chain of Tryptophan Using Triarylbismuthines
  作者：Adrien Le Roch、Hwai‐Chien Chan、Alexandre Gagnon

  DOI：10.1002/ejoc.202000667

  日期：2020.9.30

  for the regioselective N‐arylation of the indole side chain of tryptophan using triarylbismuth reagents as the arylating agent is reported. The reaction is catalyzed by copper(II) acetate in the presence of an organic base. The protocol allows the installation of electron rich or poor aryl groups with substituents at any position, shows excellent scope and functional group compatibility, and retains

  报道了使用三芳基铋试剂作为芳基化剂的色氨酸吲哚侧链区域选择性N-芳基化的简单协议。在有机碱的存在下，该反应由乙酸铜（II）催化。该方案允许在任何位置安装带有取代基的富电子或弱芳基，显示出极好的范围和官能团相容性，并保留了立体中心的完整性。
• Copper‐Promoted O‐Arylation of the Phenol Side Chain of Tyrosine Using Triarylbismuthines
  作者：Adrien Le Roch、Martin Hébert、Alexandre Gagnon

  DOI：10.1002/ejoc.202000790

  日期：2020.9.7

  for the O‐arylation of the side chain of tyrosine using triarylbismuth reagents is reported. The reaction is performed in dichloromethane under oxygen at 50 °C in the presence of pyridine, is promoted by copper diacetate, shows excellent scope and functional group tolerance, and retains the integrity of the chiral center. The reactivity of other amino acids possessing a nucleophilic side chain under these

  报道了使用三芳基铋试剂对酪氨酸侧链进行O-芳基化的方法。该反应在吡啶存在下于氧气中于50°C的氧气中于二氯甲烷中进行，由二乙酸铜促进，显示出极好的范围和官能团耐受性，并保留了手性中心的完整性。研究了在这些条件下具有亲核侧链的其他氨基酸的反应性。可以实现含酪氨酸的二肽和三肽的O-酰化。
• Tryptophan N 1-Alkylation: Quick and Simple Access to Diversely Substituted Tryptophans
  作者：Lukas Junk、Emanuel Papadopoulos、Uli Kazmaier

  DOI：10.1055/a-1404-5079

  日期：2021.7

  derivatization of peptides for pharmaceutical applications. We herein present a new protocol to alkylate the indole-nitrogen (N1) of N α-protected tryptophans. This method provides quick and epimerization-free access to tryptophan derivatives, which can directly be incorporated into peptides. Depending on the functionalities introduced in the side chain, different options for the late-stage modification of peptides

  氨基酸侧链的多样化是用于药物应用的肽的合成和衍生化中的主要挑战。我们在这里提出了一种新的方案，以烷基化Nα保护的色氨酸的吲哚氮（N1）。该方法提供了快速，无差向异构的色氨酸衍生物的途径，色氨酸衍生物可以直接掺入肽中。取决于侧链中引入的功能，肽的后期修饰的不同选择是可能的。
• An alternative and facile purification procedure of amidation and esterification reactions using a medium fluorous Mukaiyama reagent
  作者：Masato Matsugi、Misaki Suganuma、Shoko Yoshida、Shohei Hasebe、Yoko Kunda、Kotaro Hagihara、Sayaka Oka

  DOI：10.1016/j.tetlet.2008.09.016

  日期：2008.11

  convenient methodology for the separation of a fluorous by-product using fluorous chemistry is described. A Mukaiyama coupling reagent bearing a medium fluorous tag, between 40% and 60% fluorine by weight, can be effectively separated from non-fluorous components by increasing the water content of the crude reaction mixture and subsequent filtration. Additional fluorous solid phase extraction is not necessary

  描述了一种使用氟化学分离氟副产物的简便方法。通过增加粗反应混合物的水含量并随后过滤，可以有效地将氟含量在40％至60％之间的带有中等氟标签的Mukaiyama偶联剂与非氟组分有效地分离。不需要额外的氟固相萃取。
• 一种手性α-甲基芳乙胺的制备方法
  申请人：暨明医药科技（苏州）有限公司

  公开号：CN112920053B

  公开（公告）日：2022-07-01

  本发明提供了一种手性α‑甲基芳乙胺的制备方法，涉及有机合成药物技术领域。本发明使用Boc‑氨基酸甲酯作为起始原料，经还原得到Boc‑氨基醇，与氯化亚砜反应后，经高碘酸钠氧化得到磺酰胺化合物，再经路易斯酸促进的硼氢化钠还原，酸性条件脱除保护基得到目标化合物。本方法原料廉价易得，使用手性原料得到单一的光学异构体产物，克服了柱色谱拆分问题，避免大量固废和异构体的产生，提高了原子经济性，产物纯度高，收率高，有效的降低了生产成本。而且本发明使用温和的还原体系来替代原来的高压氢化反应，工艺操作相对简单，更适合规模化工业生产。