Boc-顺式-3-羟基-L-脯氨酸 | 186132-96-7

• 物质功能分类: 医药中间体
• 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: Boc-顺式-3-羟基-L-脯氨酸
• 中文别名: (2S,3R)-3-羟基-1,2-吡咯烷二甲酸1-叔丁酯；(2S,3R)-3-羟基-1,2-吡咯烷二甲酸 1-叔丁酯
• 英文名称: (2S,3R)-1-(tert-butoxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid
• 英文别名: (2S,3R)-3-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
• CAS: 186132-96-7
• 化学式: C₁₀H₁₇NO₅
• 分子量: 231.249
• InChiKey: JLDHXHPQMBNKMC-RQJHMYQMSA-N

物化性质

• 沸点：
  390.9±42.0 °C(Predicted)
• 密度：
  1.312±0.06 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  5

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：
  储存温度应保持在2-8°C，需干燥并密封保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Boc-cis-3-hydroxy-l-proline
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-cis-3-hydroxy-l-proline
CAS number: 186132-96-7

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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: C10H17NO5
Molecular weight: 231.2

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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：

  Boc-顺式-3-羟基-L-脯氨酸 在 N-甲基吗啉 、 氟化铵 、 sodium hydroxide 、 N-羟基丁二酰亚胺 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 17.92h， 生成 (2S)-2-[[(5S,8R)-5-[[(2S,3R)-1-(2-氨基-3-羟基丙酰基)-3-羟基吡咯烷-2-羰基]氨基]-13,15-二羟基-16-甲基-2,6-二氧代3-氧杂-10-硫杂-7-氮杂双环[10.4.0]十六-1(16),12,14-三烯-8-羰基]氨基]丙酸
  参考文献：
  名称：

  环丁胺的全合成

  摘要：

  描述了从硫链霉菌分离出的一种新的DNA促旋酶抑制剂cyclothialidine（1）的总合成。通过制备内酯13（方案2）来测试合成的概念，该内酯13包含特征性双环核心实体1。合成1的关键特征是：通过两个连续的曼尼希氨基甲基化/氢化序列，由3,5-二羟基苯甲酸（19）制备3,5-二羟基-2,6-二甲基苯甲酸（23）；酯衍生物的苄基N-溴琥珀酰亚胺溴化25其及其随后与Boc-Ser-Cys-OMe的偶联（11）；使用优选的Mitsunobu条件将ω-羟基酸29 29环化为12元内酯30；的肽侧链的完成1使用Boc策略（路线4）。通过外消旋物通过含有脂肪酶催化的对映体特异性乙酸酯水解的有效反应序列拆分，得到旋光纯的顺式-N-（叔丁氧基羰基）-3-羟基-L-脯氨酸（（-）- 14）（方案3） 。自然结构1通过与合成材料比较确认。描述的合成路线还提供方便的类似物1，例如经由中间30。

  DOI：

  10.1002/hlca.19960790816
• 作为产物：
  描述：

  2-benzyl 1-(tert-butyl)(2S,3R)-3-hydroxypyrrolidine-1,2-dicarboxylate 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 0.5h， 以89%的产率得到Boc-顺式-3-羟基-L-脯氨酸
  参考文献：
  名称：

  环丁胺的全合成

  摘要：

  描述了从硫链霉菌分离出的一种新的DNA促旋酶抑制剂cyclothialidine（1）的总合成。通过制备内酯13（方案2）来测试合成的概念，该内酯13包含特征性双环核心实体1。合成1的关键特征是：通过两个连续的曼尼希氨基甲基化/氢化序列，由3,5-二羟基苯甲酸（19）制备3,5-二羟基-2,6-二甲基苯甲酸（23）；酯衍生物的苄基N-溴琥珀酰亚胺溴化25其及其随后与Boc-Ser-Cys-OMe的偶联（11）；使用优选的Mitsunobu条件将ω-羟基酸29 29环化为12元内酯30；的肽侧链的完成1使用Boc策略（路线4）。通过外消旋物通过含有脂肪酶催化的对映体特异性乙酸酯水解的有效反应序列拆分，得到旋光纯的顺式-N-（叔丁氧基羰基）-3-羟基-L-脯氨酸（（-）- 14）（方案3） 。自然结构1通过与合成材料比较确认。描述的合成路线还提供方便的类似物1，例如经由中间30。

  DOI：

  10.1002/hlca.19960790816

文献信息

• [EN] HEPATITIS C VIRUS INHIBITORS<br/>[FR] INHIBITEURS DU VIRUS DE L'HEPATITE C
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2003099274A1

  公开（公告）日：2003-12-04

  Hepatitis C virus inhibitors are disclosed having the general formula:(I) wherein R1, R2, R3, R', B, Y and X are described in the description. Compositions comprising the compounds and methods for using the compounds toinhibit HCV are also disclosed.

  丙型肝炎病毒抑制剂公开了具有以下通式：其中R1、R2、R3、R'、B、Y和X在描述中有所描述。还公开了包含该化合物的组合物以及使用该化合物抑制HCV的方法。
• [EN] HETEROCYCLIC COMPOUNDS FOR USE IN THE TREATMENT OF CANCER<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES DESTINÉS À ÊTRE UTILISÉS DANS LE TRAITEMENT DU CANCER
  申请人：ARTIOS PHARMA LTD

  公开号：WO2021028643A1

  公开（公告）日：2021-02-18

  The application relates to heterocyclic amide derivatives and their use in the treatment and prophylaxis of cancer, and to compositions containing said derivatives and processes for their preparation. (Formula (I))

  该申请涉及杂环酰胺衍生物及其在癌症治疗和预防中的应用，以及含有这些衍生物的组合物和其制备方法。(化学式(I))
• [EN] SUBSTITUTED HETEROCYCLIC SULFONAMIDE COMPOUNDS USEFUL AS TRPA1 MODULATORS<br/>[FR] COMPOSÉS DE SULFONAMIDE HÉTÉROCYCLIQUES SUBSTITUÉS UTILES COMME MODULATEURS DE TRPA1
  申请人：HOFFMANN LA ROCHE

  公开号：WO2015052264A1

  公开（公告）日：2015-04-16

  The invention is concerned with the compounds of formula I or II: and salts thereof. In addition, the present invention relates to methods of manufacturing and methods of using the compounds of formula I or II as well as pharmaceutical compositions containing such compounds. The compounds may be useful in treating diseases and conditions mediated by TRPA1, such as pain.

  本发明涉及式I或II的化合物及其盐。此外，本发明还涉及制备这些化合物的方法以及使用这些化合物的方法，以及含有这些化合物的药物组合物。这些化合物可能对治疗由TRPA1介导的疾病和状况，如疼痛，具有用途。
• [EN] INDOLE COMPOUNDS OR ANALOGUES THEREOF USEFUL FOR THE TREATMENT OF AGE-RELATED MACULAR DEGENERATION (AMD)<br/>[FR] COMPOSÉS INDOLIQUES OU ANALOGUES DE CEUX-CI UTILES DANS LE TRAITEMENT DE LA DÉGÉNÉRESCENCE MACULAIRE LIÉE À L'ÂGE (DMLA)
  申请人：NOVARTIS AG

  公开号：WO2012093101A1

  公开（公告）日：2012-07-12

  The present invention provides a compound of formula (I): a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

  本发明提供了一种公式(I)的化合物：一种制造本发明化合物的方法及其治疗用途。本发明进一步提供了一种药物活性剂的组合物和一种药物组合物。
• [EN] BENZIIMIDAZOLE AND IMIDAZOPYRIDINE DERIVATIVES AS SODIUM CHANNEL MODULATORS<br/>[FR] DÉRIVÉS D'IMIDAZOPYRIDINE ET DE BENZIIMIDAZOLE EN TANT QUE MODULATEURS DU CANAL SODIUM
  申请人：PFIZER

  公开号：WO2013114250A1

  公开（公告）日：2013-08-08

  The invention relates to benzimidazole and imidazopyridine derivatives, to their use in medicine, to compositions containing them, to processes for their preparation and to intermediates used in such processes. More particularly the invention relates to new Nav1.8 modulators of formula (I) or pharmaceutically acceptable salts thereof, wherein R1, R2, R3, R4, R5, R6, R7. X and Y are as defined in the description. Nav1.8 modulators are potentially useful in the treatment of a wide range of disorders, particularly pain.

  这项发明涉及苯并咪唑和咪唑吡啶衍生物，它们在药物中的应用，含有它们的组合物，它们的制备方法以及用于这些方法的中间体。更具体地，该发明涉及公式(I)的新Nav1.8调节剂或其药用盐，其中R1、R2、R3、R4、R5、R6、R7、X和Y如描述中所定义。Nav1.8调节剂在治疗各种疾病，特别是疼痛方面，具有潜在的用途。