N-carbamoyl-S-tert-butyl-L-α-methylcysteine | 634152-60-6

• 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
• 英文名称: N-carbamoyl-S-tert-butyl-L-α-methylcysteine
• 英文别名: (R)-3-(tert-butylthio)-2-methyl-2-ureidopropanoic acid；N-carbamoyl-S-tert-butyl-α-methylcysteine；N-carbamoyl-S-tert-butyl-alpha-methylcysteine；(2R)-3-tert-butylsulfanyl-2-(carbamoylamino)-2-methylpropanoic acid
• CAS: 634152-60-6
• 化学式: C₉H₁₈N₂O₃S
• 分子量: 234.32
• InChiKey: OIOPFLKIZNJQQH-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  118
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-carbamoyl-S-tert-butyl-L-α-methylcysteine 在 盐酸 作用下， 反应 72.0h， 以100%的产率得到2-甲基-L-半胱氨酸盐酸盐
  参考文献：
  名称：

  Largazole and Analogues with Modified Metal-Binding Motifs Targeting Histone Deacetylases: Synthesis and Biological Evaluation

  摘要：

  The histone deacetylase inhibitor largazole 1 was synthesized by a convergent approach that involved several efficient and high yielding single pot multistep protocols. Initial attempts using tert-butyl as thiol protecting group proved problematic, and synthesis was accomplished by switching to the trityl protecting group. This synthetic protocol provides a convenient approach to many new largazole analogues. Three side chain analogues with multiple heteroatoms for chelation with Zn2+ were synthesized, and their biological activities were evaluated. They were less potent than largazole 1 in growth inhibition of HCT116 colon carcinoma cell line and in inducing increases in global H3 acetylation. Largazole 1 and the three side chain analogues had no effect on HDAC6, as indicated by the lack of increased acetylation of alpha-tubulin.

  DOI：

  10.1021/jm200432a
• 作为产物：
  描述：

  5-tert-butylthiomethyl-5-methylhydantoin 在 sodium hydroxide 、 manganese(II) sulfate 、 sodium chloride 作用下， 反应 46.5h， 生成 N-carbamoyl-S-tert-butyl-L-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

文献信息

• 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。
• PROCESS FOR PRODUCING OPTICALLY ACTIVE ALPHA-METHYLCYSTEINE DERIVATIVE
  申请人：Ohishi Takahiro

  公开号：US20100197934A1

  公开（公告）日：2010-08-05

  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、廉价的原料中生产L-或D-光学活性α-甲基半胱氨酸衍生物或其盐，该衍生物是一种有用的药物中间体。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，使用外消旋N-氨基甲基半胱氨酸衍生物或其盐与咪唑二酮酶D-选择性环化，以产生D-5-甲基-5-硫甲基咪唑二酮衍生物或其盐和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，并进行水解。
• Process for producing optically active α-methylcysteine derivative
  申请人：Kaneka Corporation

  公开号：US08993800B2

  公开（公告）日：2015-03-31

  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，利用咪唑酶D-选择性环化混合的N-碳酰基-α-甲基半胱氨酸衍生物或其盐，以产生D-5-甲基-5-硫甲基咪唑烷衍生物或其盐和N-碳酰基-α-甲基-L-半胱氨酸衍生物或其盐，然后对氨基和硫原子进行去保护和水解。
• PROCESS FOR PRODUCING OPTICALLY ACTIVE alpha-METHYLCYSTEINE DERIVATIVE
  申请人：KANEKA CORPORATION

  公开号：EP1550725A1

  公开（公告）日：2005-07-06

  The present invention provides a simple industrial process for producing an L- or D-optionally 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工艺，可以用容易获得的廉价原料生产 L-或 D-选择活性 α-甲基半胱氨酸衍生物或其盐，这种衍生物是一种有用的医药中间体。 在生产具有 L 或 D 选择活性的 α-甲基半胱氨酸衍生物或其盐的工艺中，外消旋 N-氨基甲酰基-α-甲基半胱氨酸衍生物或其盐与海因酶进行 D 选择性环化，生成 D-5-甲基-5-硫代甲基海因衍生物或其盐和 N-氨基甲酰基-α-甲基-L-半胱氨酸衍生物或其盐，然后对其氨基和硫原子进行脱保护和水解。