N-tosyl-D,L-phenylglycine

• 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
• 英文名称: N-tosyl-D,L-phenylglycine
• 英文别名: N-tosyl-D-phenylglycine；N-(Toluene-4-sulfonyl)phenylglycine；2-[2-(4-Methylphenyl)sulfonylanilino]acetic acid
• 化学式: C₁₅H₁₅NO₄S
• 分子量: 305.354
• InChiKey: SBDCBTPPHAUCTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  91.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-tosyl-D,L-phenylglycine 、 1-(3-morpholinocarbonyl-1-phenylpropenyl)amino-3-phenyl-2-propanol 在 盐酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 氮气 、 水 为溶剂， 以67%的产率得到(2RS)-1-[(1SR)-3-morpholino-1-phenylpropyl]amino-3-phenyl-2-propanol
  参考文献：
  名称：

  EP1118611

  摘要：

  公开号：

文献信息

• PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE PIPERIDINE COMPOUND
  申请人：Mitsubishi Tanabe Pharma Corporation

  公开号：EP2022782A1

  公开（公告）日：2009-02-11

  The present invention relates to a method for preparing a syn-form piperidine compound represented by general formula [I]: wherein, bold lines represent bonds in which substituents at positions 2 and 4 of a piperidine ring are in the syn configuration, and the other symbols have the same meaning as defined below, or a salt thereof, comprising: reducing a compound represented by general formula [II]: wherein, ring A represents an optionally substituted benzene ring, R2 represents a hydrogen atom, an optionally substituted hydroxyl group, an optionally substituted amino group, an optionally substituted alkyl group, a substituted carbonyl group or a halogen atom, and M represents an alkaline metal or hydrogen atom.

  本发明涉及一种制备由通用式[I]表示的同构吡啶化合物的方法：其中，粗线表示吡啶环的2位和4位取代基处于同构构象，其他符号的含义如下定义，或其盐，包括：还原由通用式[II]表示的化合物：其中，环A表示一个可选择取代的苯环，R2表示氢原子、可选择取代的羟基、可选择取代的氨基、可选择取代的烷基、取代的羰基或卤素原子，M表示碱金属或氢原子。
• Compounds which inhibit leukocyte adhesion mediated by VLA-4
  申请人：——

  公开号：US20030166575A1

  公开（公告）日：2003-09-04

  Disclosed are compounds which bind VLA-4. Certain of these compounds also inhibit leukocyte adhesion and, in particular, leukocyte adhesion mediated by VLA-4. Such compounds are useful in the treatment of inflammatory diseases in a mammalian patient, e.g., human, such as asthma, Alzheimer's disease, atherosclerosis, AIDS dementia, diabetes, inflammatory bowel disease, rheumatoid arthritis, tissue transplantation, tumor metastasis and myocardial ischemia. The compounds can also be administered for the treatment of inflammatory brain diseases such as multiple sclerosis.

  本发明涉及一种与VLA-4结合的化合物。其中某些化合物还能抑制白细胞黏附，特别是由VLA-4介导的白细胞黏附。这样的化合物可用于治疗哺乳动物患者，例如人类，的炎症性疾病，如哮喘、阿尔茨海默病、动脉粥样硬化、艾滋病痴呆、糖尿病、炎性肠病、类风湿性关节炎、组织移植、肿瘤转移和心肌缺血。这些化合物还可用于治疗多发性硬化等炎症性脑部疾病。
• METHOD FOR PREPARING OPTICALLY ACTIVE PIPERIDINE COMPOUNDS
  申请人：Matsumae Hiroaki

  公开号：US20090198052A1

  公开（公告）日：2009-08-06

  The present invention relates to a method for preparing a syn-form piperidine compound represented by general formula [I]: wherein, bold lines represent bonds in which substituents at positions 2 and 4 of a piperidine ring are in the syn configuration, and the other symbols have the same meaning as defined below, or a salt thereof, comprising: reducing a compound represented by general formula [II]: wherein, ring A represents an optionally substituted benzene ring, R 2 represents a hydrogen atom, an optionally substituted hydroxyl group, an optionally substituted amino group, an optionally substituted alkyl group, a substituted carbonyl group or a halogen atom, and M represents an alkaline metal or hydrogen atom.

  本发明涉及一种制备一种由通式[I]表示的syn型哌啶化合物的方法：其中，粗线表示哌啶环的2和4位取代基处为syn构型，其他符号的含义如下所定义，或其盐，包括：还原由通式[II]表示的化合物：其中，环A表示可选取代的苯环，R2表示氢原子、可选取代的羟基、可选取代的氨基、可选取代的烷基、取代的羰基或卤素原子，M表示碱金属或氢原子。
• Process for preparing optically active piperazine derivatives and intermediates for preparation
  申请人：YAMAKAWA CHEMICAL INDUSTRY CO., LTD.

  公开号：EP0710652A2

  公开（公告）日：1996-05-08

  Process for preparing optically active 2-piperazinecarboxylic acid derivatives, particularly S-enantiomer thereof, in high yield and high optical purity on industrial scale. As the optical resolving agents, easily accessible sulfonamides derived from selected optically active amino acids, such as N-tosyl-L-phenylalanine, N-tosyl-D-phenylglycine, N-tosyl-L-alanine or N-tosyl-L-valine, give excellent results. These resolving agents are stable and easily recovered from the reaction mixture and reused. Resolved 2-piperazinecarboxylic acid derivatives are preferably isolated as 4-t-butoxycarbonyl (Boc) derivatives. Diastereomeric salts (an example being shown below) formed as the intermediates of resolution are novel. [In the formula "Ar" stands for a phenyl or naphthyl group which may be substituted with one to three C1-C6 alkyl groups, halogen atoms, nitro or alkoxy groups; and n=0 or 1.]

  在工业规模上以高产率和高光学纯度制备光学活性 2-哌嗪羧酸衍生物，特别是其 S-对映体的工艺。作为光学分解剂，从选定的光学活性氨基酸（如 N-对甲苯磺酰基-L-苯丙氨酸、N-对甲苯磺酰基-D-苯甘氨酸、N-对甲苯磺酰基-L-丙氨酸或 N-对甲苯磺酰基-L-缬氨酸）中提取的易于获得的磺酰胺类物质效果极佳。这些分解剂非常稳定，很容易从反应混合物中回收并重复使用。溶解后的 2-哌嗪甲酸衍生物最好以 4-叔丁氧羰基（Boc）衍生物的形式分离出来。作为分解中间体形成的非对映异构盐（如下所示的一个例子）是新颖的。 [式中 "Ar "代表苯基或萘基，可被一至三个 C1-C6 烷基、卤素原子、硝基或烷氧基取代；n=0 或 1。］
• PROCESS FOR THE PREPARATION OF OXAZOLIDINONE DERIVATIVE
  申请人：NIPPON CHEMIPHAR CO., LTD.

  公开号：EP1118611A1

  公开（公告）日：2001-07-25

  The invention relates to a process for preparing (5RS)-5-benzyl-3-[(1SR)-3-morpholino-1-phenylpropyl]-1,3-oxazolidin-2-one or its pharmacologically acceptable salt which is of value as a remedy for treatment of incontinence of urine and thamuria and which is performed by the steps of: dissolving an acid and a mixture of (2RS)-1- [(1SR)-3-morpholino-1-phenylpropyl]amino-3-phenyl-2-propanol and (2RS) -1- ((lRS,) -3-morpholino-1-phenylpropyl] amino-3-phenyl-2-propanol in a solvent to obtain a salt of the former (1SR)-compound utilizing difference of solubility between the salt of (1SR)-compound and a salt of the latter (1RS)-compound; bringing a basic compound into contact with the salt of (1SR)-compound to produce a free (1SR)-compound; reacting thus produced (2RS)-1-[(1SR)-3-morpholino-1-phenylpropyl]amino-3-phenyl-2-propanol with a compound having the formula (I):         R2C=O     (I) wherein R represents a chlorine atom, an alkoxy group, an aryloxy group or an amino group, or a chloroformic acid ester; and cyclizing the resulting product.

  本发明涉及一种制备(5RS)-5-苄基-3-[(1SR)-3-吗啉基-1-苯基丙基]-1,3-恶唑啉-2-酮或其药理上可接受的盐的工艺，该工艺具有治疗尿失禁和thamuria的价值，其步骤如下： 将酸和(2RS)-1-[(1SR)-3-吗啉基-1-苯丙基]氨基-3-苯基-2-丙醇和(2RS)-1-((lRS,)-3-吗啉基-1-苯丙基]氨基-3-苯基-2-丙醇的混合物溶解在溶剂中，利用(1SR)-化合物的盐和(1RS)-化合物的盐之间的溶解度差异，得到前者(1SR)-化合物的盐； 将碱性化合物与(1SR)-化合物的盐接触，生成游离的(1SR)-化合物； 将生成的(2RS)-1-[(1SR)-3-吗啉基-1-苯基丙基]氨基-3-苯基-2-丙醇与式(I)化合物反应： R2C=O (I) 其中 R 代表氯原子、烷氧基、芳氧基或氨基或氯甲酸酯；以及 使所得产物环化。