(1R,2R,4R)-N-Boc-1-氨基-2-羟基环戊烷-4-羧酸甲酯 | 321744-18-7

• 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: (1R,2R,4R)-N-Boc-1-氨基-2-羟基环戊烷-4-羧酸甲酯
• 中文别名: (1R,2R,4R)-N-BOC-1-氨基-2-羟基环戊烷-4-甲酸甲酯
• 英文名称: (1R,3R,4R)-3-tert-butoxycarbonylamino-4-hydroxycyclopentanecarboxylic acid methyl ester
• 英文别名: methyl (1R,3R,4R)-3-((tert-butoxycarbonyl)amino)-4-hydroxycyclopentane-1-carboxylate；(1R,2R,4R)-N-boc-1-amino-2-hydroxycyclopentane-4-carboxylic acid methyl ester；Methyl (1R,3R,4R)-3-[(tert-butoxycarbonyl)amino]-4-hydroxycyclopentane-1-carboxylate；methyl (1R,3R,4R)-3-hydroxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopentane-1-carboxylate
• CAS: 321744-18-7
• 化学式: C₁₂H₂₁NO₅
• 分子量: 259.302
• InChiKey: SSATZBUCOTXXGA-IWSPIJDZSA-N

物化性质

• 沸点：
  402.56°C (rough estimate)
• 密度：
  1.1623 (rough estimate)
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 安全说明：
  S24/25

SDS

Name:	(1R 2R 4R)-N-BOC-1-Amino-2-hydroxycyclopentane-4-carboxylic acid Material Safety Data Sheet
Synonym:	Methyl (1R,3R,4R)-N-BOC-3-amino-4-hydroxycyclopentanecarboxylate
CAS:	321744-18-7

Section 1 - Chemical Product MSDS Name:(1R 2R 4R)-N-BOC-1-Amino-2-hydroxycyclopentane-4-carboxylic acid Material Safety Data Sheet
Synonym:Methyl (1R,3R,4R)-N-BOC-3-amino-4-hydroxycyclopentanecarboxylate

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
321744-18-7	(1R,2R,4R)-N-BOC-1-Amino-2-hydroxycycl	95	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. May be harmful if inhaled.
Chronic:
No information found.

---

Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

---

Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

---

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

---

Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

---

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 321744-18-7: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C12H21NO5
Molecular Weight: 259.3

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not currently available.
Conditions to Avoid:
Incompatible materials, dust generation.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 321744-18-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(1R,2R,4R)-N-BOC-1-Amino-2-hydroxycyclopentane-4-carboxylic - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

---

Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 321744-18-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 321744-18-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 321744-18-7 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (1R,2R,4R)-N-Boc-1-氨基-2-羟基环戊烷-4-羧酸甲酯 在 lithium hydroxide monohydrate 作用下， 以 甲醇 、 水 为溶剂， 反应 16.0h， 生成 (1R,3R,4R)-3-((tert-butoxycarbonyl)amino)-4-hydroxycyclopentane-1-carboxylic acid
  参考文献：
  名称：

  [EN] COMPOUNDS AND COMPOSITIONS USEFUL FOR TREATING DISORDERS RELATED TO NTRK
  [FR] COMPOSÉS ET COMPOSITIONS UTILES POUR TRAITER DES TROUBLES ASSOCIÉS AU GÈNE NTRK

  摘要：

  这项发明涉及对NTRK的抑制剂，对野生型NTRK及其耐药突变体具有活性。

  公开号：

  WO2017035354A1
• 作为产物：
  描述：

  (1S,4R)-4-甲基环戊-2-烯甲酸甲酯盐酸盐 在 4-二甲氨基吡啶 、 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 (+)-1,2-bis((2R,5R)-2,5-dimethylphospholano)benzene(cyclooctadiene)rhodium(I) tetrafluoroborate 、 TEA 、 氢气 、 sodium methylate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 90.0 ℃ 、517.11 kPa 条件下， 反应 331.0h， 生成 (1R,2R,4R)-N-Boc-1-氨基-2-羟基环戊烷-4-羧酸甲酯
  参考文献：
  名称：

  An efficient route to all eight stereoisomers of a tri-functionalised cyclopentane scaffold for drug discovery

  摘要：

  A route to all eight stereoisomers of 3-(tert-butoxycarbonylamino)-4-hydroxycyclopentanecarboxylic acid methyl ester is presented; these products should prove to be valuable scaffolds in pharmaceutical discovery. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00108-2

文献信息

• Antibacterial Optimization of 4-Aminothiazolyl Analogues of the Natural Product GE2270 A: Identification of the Cycloalkylcarboxylic Acids
  作者：Matthew J. LaMarche、Jennifer A. Leeds、Kerri Amaral、Jason T. Brewer、Simon M. Bushell、Janetta M. Dewhurst、JoAnne Dzink-Fox、Eric Gangl、Julie Goldovitz、Akash Jain、Steve Mullin、Georg Neckermann、Colin Osborne、Deborah Palestrant、Michael A. Patane、Elin M. Rann、Meena Sachdeva、Jian Shao、Stacey Tiamfook、Lewis Whitehead、Donghui Yu

  DOI：10.1021/jm200938f

  日期：2011.12.8

  4-Aminothiazolyl analogues of the antibiotic natural product GE2270 A (1) were designed, synthesized, and optimized for their activity against Gram positive bacterial infections. Optimization efforts focused on improving the physicochemical properties (e.g., aqueous solubility and chemical stability) of the 4-aminothiazolyl natural product template while improving the in vitro and in vivo antibacterial

  设计，合成和优化了抗生素天然产物GE2270 A（1）的4-氨基噻唑类似物，以抵抗革兰氏阳性细菌感染。优化工作着重于提高4-氨基噻唑基天然产物模板的理化性质（例如，水溶性和化学稳定性），同时提高体外和体内的抗菌活性。定义了结构活性关系，并且溶解度和功效谱比以前的类似物和1有所改善。这些研究确定了具有环烷基羧酸侧链的新型，有效，可溶和有效的伸长因子Tu抑制剂，并最终选择了开发候选酰胺48。和氨基甲酸酯58。
• Use of hydrolases for the synthesis of cyclic amino acids
  作者：Richard C Lloyd、Michael C Lloyd、Mark E.B Smith、Karen E Holt、Jonathan P Swift、Philip A Keene、Stephen J.C Taylor、Raymond McCague

  DOI：10.1016/j.tet.2003.10.116

  日期：2004.1

  The synthesis of several cyclic amino acids that have all the necessary structural features to make them ideal scaffolds for use in medicinal chemistry is described. A key step in each synthesis is the use of hydrolase enzymes to define a chiral centre. In order to elaborate these building blocks into more complex molecules, crystallization and asymmetric hydrogenation were used to define further stereocentres

  描述了具有所有必要结构特征以使其成为用于药物化学的理想支架的几种环状氨基酸的合成。每个合成过程中的关键步骤是使用水解酶来定义手性中心。为了将这些结构单元详细化为更复杂的分子，使用了结晶和不对称氢化来定义进一步的立体中心。
• Highly selective directed hydrogenation of enantiopure 4-( tert -butoxycarbonylamino)cyclopent-1-enecarboxylic acid methyl esters
  作者：Mark E.B Smith、Nadine Derrien、Michael C Lloyd、Stephen J.C Taylor、David A Chaplin、Raymond McCague

  DOI：10.1016/s0040-4039(00)02210-3

  日期：2001.2

  The use of both N-tert-butoxycarbonylamino- and hydroxyl-directed hydrogenation methodology to yield essentially single diastereomers of 3-(tert-butoxycarbonylamino)-4-hydroxycyclopentanecarboxylic acid methyl esters and 3-(tert-butoxycarbonylamino)cyclopentanecarboxylic acid methyl esters is described. These results incorporate the first reported carbamate-directed hydrogenations of functionalised

  同时使用的ñ -叔叔丁氧羰和羟基定向加氢方法得到的3-基本上单非对映体（叔丁氧基羰基）-4- hydroxycyclopentanecarboxylic酸甲酯和3-（叔丁氧基羰基）环戊烷羧酸甲酯进行说明。这些结果结合了第一个报道的官能化环戊烯的氨基甲酸酯定向加氢反应。
• Compounds and compositions useful for treating disorders related to NTRK
  申请人：BLUEPRINT MEDICINES CORPORATION

  公开号：US10017512B2

  公开（公告）日：2018-07-10

  This disclosure relates to inhibitors of NTRK that are active against wild-type NTRK and its resistant mutants, such as compounds of Formula (I):

  本公开涉及对野生型 NTRK 及其抗性突变体有活性的 NTRK 抑制剂，如式 (I) 化合物：
• COMPOUNDS AND COMPOSITIONS USEFUL FOR TREATING DISORDERS RELATED TO NTRK
  申请人：BLUEPRINT MEDICINES CORPORATION

  公开号：US20170066773A1

  公开（公告）日：2017-03-09

  This invention relates to inhibitors of NTRK that are active against wild-type NTRK and its resistant mutants.