S-tert-butyl-D-α-methylcysteine | 634152-62-8

• 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: S-tert-butyl-D-α-methylcysteine
• 英文别名: L-2-tert-butylthiomethylalanine；S-tert-butyl-alpha-methyl-D-cysteine；(2S)-2-amino-3-tert-butylsulfanyl-2-methylpropanoic acid
• CAS: 634152-62-8
• 化学式: C₈H₁₇NO₂S
• 分子量: 191.294
• InChiKey: NMJNPLIFGMSGNZ-MRVPVSSYSA-N

物化性质

• 沸点：
  301.8±37.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  88.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  S-tert-butyl-D-α-methylcysteine 在 盐酸 作用下， 反应 45.0h， 以96.7%的产率得到2-甲基-D-半胱氨酸盐酸盐
  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：

  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

文献信息

• PROCESS FOR PRODUCING L-a-METHYLCYSTEINE DERIVATIVE
  申请人：KANEKA CORPORATION

  公开号：EP1541692A1

  公开（公告）日：2005-06-15

  A process for easily producing an L-α-methylcysteine derivative or its salt, which is useful as a drug intermediate, from a cheap easily procurable raw material through an enzymatic D-stereoselective hydrolysis of racemic 5-halomethyl-5-methyl-hydantoin. L-α-methylcysteine derivative or its salt is produced by converting racemic 5-halomethyl-5-methylhydantoin to L-5-halomethyl-5-methylhydantoin through an enzymatic D-stereoselective hydrolysis, reacting the L-5-halomethyl-5-methylhydantoin with a sulfurizing agent into L-5-methyl-5-thiomethylhydantoin and hydrolyzing the L-5-methyl-5-thiomethylhydantoin.

  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。
• 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：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。