5-tert-butylthiomethyl-5-methylhydantoin | 33109-53-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 5-tert-butylthiomethyl-5-methylhydantoin
• 英文别名: 5-(tert-butylthiomethyl)-5-methylimidazolidine-2,4-dione；5-tert-butylsulfanylmethyl-5-methyl-imidazolidine-2,4-dione；D-5-tert-butylthiomethyl-5-methylhydantoin；D-5-methyl-5-tert-butylthiomethylhydantoin；L-5-methyl-5-tert-butylthiomethylhydantoin；5-(tert-butylsulfanylmethyl)-5-methylimidazolidine-2,4-dione
• CAS: 33109-53-4
• 化学式: C₉H₁₆N₂O₂S
• 分子量: 216.304
• InChiKey: CLCLQDMQZNAPJH-UHFFFAOYSA-N

物化性质

• 熔点：
  208-210 °C(Solv: ethanol (64-17-5))
• 密度：
  1.118±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  83.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-tert-butylthiomethyl-5-methylhydantoin 在 lithium hydroxide 、 sodium hydroxide 、 manganese(II) sulfate 、 sodium chloride 作用下， 反应 46.5h， 生成 S-tert-butyl-D-α-methylcysteine
  参考文献：
  名称：

  乙内酰脲酶对d-和l-α-甲基半胱氨酸的对映选择性合成

  摘要：

  描述了可扩展的和成本有效的合成d-和l-α-甲基半胱氨酸。一个关键步骤是d-选择性环化ñ -氨基甲酰基小号-叔丁基的d，l-α -甲基半胱氨酸由乙内酰脲催化。d -5-叔-Butylthiomethyl -5-甲基乙和ñ -氨基甲酰基小号-叔丁基-1-α甲基半胱氨酸具有优异的产率和光学纯度获得，并且这些化合物很容易通过过滤分离。叔丁基水解和裂解后，得到d-和l-α-甲基半胱氨酸盐酸盐。

  DOI：

  10.1016/j.tetlet.2007.03.040
• 作为产物：
  描述：

  叔丁基硫醇 、 5-(氯甲基)-5-甲基咪唑烷-2,4-二酮 以 sodium hydroxide 为溶剂， 以58.6%的产率得到5-tert-butylthiomethyl-5-methylhydantoin
  参考文献：
  名称：

  PROCESS FOR PRODUCING L-a-METHYLCYSTEINE DERIVATIVE

  摘要：

  一种生产L-α-甲基半胱氨酸衍生物或其盐的方法，该衍生物在药物中间体中有用，通过酶催化的D-立体选择性水解5-卤代甲基-5-甲基-异嘧啶的混合物，从便宜易得的原料中轻松生产。将混合物转化为L-5-卤代甲基-5-甲基-异嘧啶，然后将其与硫化剂反应成L-5-甲基-5-硫代甲基-异嘧啶，最后对L-5-甲基-5-硫代甲基-异嘧啶进行水解即可得到L-α-甲基半胱氨酸衍生物或其盐。

  公开号：

  EP1541692A1

文献信息

• OPTICALLY ACTIVE 3,3 -DITHIOBIS(2-AMINO-2-METHYLPROPIONI C ACID) DERIVATIVE AND PROCESS FOR PRODUCING OPTICALLY ACTIVE 2-AMINO-3-MERCAPTO-2-METHYL-PROPIONIC ACID DERIVATIVE
  申请人：KANEKA CORPORATION

  公开号：EP1666458A1

  公开（公告）日：2006-06-07

  The present invention provides a useful novel intermediate and a novel synthetic process that can highly prevent contamination by various impurities to an optically active R or S isomer of a 2-amino-3-mercapto-2-methylpropionic acid derivative or salt thereof useful as an intermediate for pharmaceuticals and the like and provides a process for easily and efficiently producing a high purity optically active R or S isomer of a 2-amino-3-mercapto-2-methylpropionic acid derivative or salt thereof on an industrial production scale. A process of producing a high purity 2-amino-3-mercapto-2-methylpropionic acid derivative or salt thereof includes reductively cleaving a sulfur-sulfur bond of an intermediate, which is a high purity optically active 3,3'-dithiobis(2-amino-2-methylpropionic acid) derivative substantially free of impurities. Thus, a resulting optically active 2-amino-3-mercapto-2-methylpropionic acid derivative can be produced without generating impurities as by-products which are difficult to remove.

  本发明提供了一种有用的新型中间体和一种新的合成过程，可以高度防止各种杂质对光学活性的2-氨基-3-巯基-2-甲基丙酸衍生物或其盐（作为药物中间体等）的R或S异构体的污染，并提供了一种在工业生产规模上轻松高效地生产高纯度光学活性的2-氨基-3-巯基-2-甲基丙酸衍生物或其盐的过程。生产高纯度的2-氨基-3-巯基-2-甲基丙酸衍生物或其盐的过程包括还原地裂解中间体的硫-硫键，该中间体是高纯度的光学活性3,3'-二硫代(2-氨基-2-甲基丙酸)衍生物，几乎不含杂质。因此，可以生产出不产生难以去除的副产物杂质的光学活性的2-氨基-3-巯基-2-甲基丙酸衍生物。
• Mass spectra of sulphur-containing amino acids and peptides
  作者：H. Nishimura、S. Tahara、H. Okuyama、J. Mitzutani

  DOI：10.1016/0040-4020(72)80032-2

  日期：1972.1

  More than twenty synthesized S-containing amino acids and peptides with biological interests, have been measured by direct inlet system of the mass spectrometer. Most of these compounds have the large molecular ion abundances and give the reproducible fragmentations. The mass spectral-fragmentation mechanisms of systematically synthesized S-alkyl-l-cysteines, S-alkyl-l-cysteine sulphoxides, S-alky

  已经通过质谱仪的直接入口系统测量了二十多种具有生物学意义的合成的含S氨基酸和肽。这些化合物大多数具有大的分子离子丰度，并产生可再现的碎片。系统合成的S-烷基-1-半胱氨酸，S-烷基-1-半胱氨酸亚砜，S-烷基-2-甲基-dl-半胱氨酸，缩水甘油基-S-烷基-dl-半胱氨酸和环状硫的质谱裂解机理提出了含氨基酸的氨基酸等。
• Process for producing optically active alpha-methylcysteine derivative
  申请人：Ohishi Takahiro

  公开号：US20060105435A1

  公开（公告）日：2006-05-18

  The present invention provides a simple industrial process for producing an L- or D-optically active α-methylcysteine derivative or its salt, which is a useful pharmaceutical intermediate, from readily available, inexpensive raw materials. In a process for producing an L- or D-optically active α-methylcysteine derivative or its salt, a racemic N-carbamoyl-α-methylcysteine derivative or its salt is D-selectively cyclized with hydantoinase to produce a D-5-methyl-5-thiomethylhydantoin derivative or its salt and an N-carbamoyl-α-methyl-L-cysteine derivative or its salt, which are then subjected to deprotection of the amino group and the sulfur atom, and hydrolysis.

  本发明提供了一种简单的工业过程，用于从易得、廉价的原材料中生产有用的药物中间体L-或D-光学活性α-甲基半胱氨酸衍生物或其盐。在生产L-或D-光学活性α-甲基半胱氨酸衍生物或其盐的过程中，利用咪唑烷酰肽酶选择性地对外消旋的N-氨基甲基半胱氨酸衍生物或其盐进行环化反应，生成D-5-甲基-5-硫甲基咪唑烷酮衍生物或其盐和N-氨基甲基-L-半胱氨酸衍生物或其盐，然后对氨基团和硫原子进行去保护作用，最后进行水解。
• Process for producing optically active alpha -methylcysteine derivative
  申请人：Ueda Makoto

  公开号：US20060172393A1

  公开（公告）日：2006-08-03

  A process for conveniently and industrially producing an optically active α-methylcysteine derivative, which is useful as an intermediate of medicines and the like, from an inexpensive and readily available material is provided. The present invention relates to a process for producing a racemic or optically active α-methylcysteine derivative including a step of hydrolyzing a racemic or optically active N-carbamyl-α-methylcysteine derivative by treating with decarbamylase, and a process for producing an optically active α-methylcysteine derivative and an optically active N-carbamyl-α-methylcysteine derivative having a configuration opposite to that of the compound including a step of stereoselectively hydrolyzing a racemic N-carbamyl-α-methylcysteine derivative by treating with decarbamylase.

  提供了一种从廉价且易得的材料中方便和工业化地生产光学活性α-甲基半胱氨酸衍生物的方法，该方法可用作药物等中间体。本发明涉及一种生产外消旋或光学活性α-甲基半胱氨酸衍生物的方法，包括通过处理脱氨基酶水解外消旋或光学活性N-碳酰基-α-甲基半胱氨酸衍生物的步骤，以及一种产生与该化合物构型相反的光学活性α-甲基半胱氨酸衍生物和光学活性N-碳酰基-α-甲基半胱氨酸衍生物的方法，包括通过处理脱氨基酶选择性地水解外消旋N-碳酰基-α-甲基半胱氨酸衍生物的步骤。
• Optically active 3,3'-dithiobis(2-amino-2methylpropionic acid) derivative and process for producing optically active 2-amino-3-mercapto-2-methylpropionic acid derivative
  申请人：Matsumoto Shingo

  公开号：US20070010689A1

  公开（公告）日：2007-01-11

  The present invention provides a useful novel intermediate and a novel synthetic process that can highly prevent contamination by various impurities to an optically active R or S isomer of a 2-amino-3-mercapto-2-methylpropionic acid derivative or salt thereof useful as an intermediate for pharmaceuticals and the like and provides a process for easily and efficiently producing a high purity optically active R or S isomer of a 2-amino-3-mercapto-2-methylpropionic acid derivative or salt thereof on an industrial production scale. A process of producing a high purity 2-amino-3-mercapto-2-methylpropionic acid derivative or salt thereof includes reductively cleaving a sulfur-sulfur bond of an intermediate, which is a high purity optically active 3,3′-dithiobis(2-amino-2-methylpropionic acid) derivative substantially free of impurities. Thus, a resulting optically active 2-amino-3-mercapto-2-methylpropionic acid derivative can be produced without generating impurities as by-products which are difficult to remove.

  本发明提供了一种有用的新型中间体和一种新型合成方法，可以高度防止各种杂质对用作制药等中间体的2-氨基-3-巯基-2-甲基丙酸衍生物或其盐的光学活性R或S异构体的污染，并提供一种在工业生产规模上轻松高效地生产高纯度光学活性R或S异构体的2-氨基-3-巯基-2-甲基丙酸衍生物或其盐的过程。生产高纯度2-氨基-3-巯基-2-甲基丙酸衍生物或其盐的过程包括还原裂解中间体的硫-硫键，该中间体是高纯度的、基本无杂质的光学活性3,3'-二硫代双(2-氨基-2-甲基丙酸)衍生物。因此，可以生产出不生成难以去除的副产物杂质的光学活性2-氨基-3-巯基-2-甲基丙酸衍生物。