2-hydroxy-2-methyl-3-(4-fluorophenylthio)-propionic acid

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-hydroxy-2-methyl-3-(4-fluorophenylthio)-propionic acid
• 英文别名: (2S)-3-(4-fluorophenyl)sulfanyl-2-hydroxy-2-methylpropanoic acid
• 化学式: C₁₀H₁₁FO₃S
• 分子量: 230.26
• InChiKey: CTYJERNWLVBMTF-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  82.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-hydroxy-2-methyl-3-(4-fluorophenylthio)-propionic acid 在 氯化亚砜 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基乙酰胺 为溶剂， 生成 N-[4-氰基-3-(三氟甲基)苯基]-3-[(4-氟苯基)磺酰基]-2-羟基-2-甲基丙酰胺
  参考文献：
  名称：

  Syntheses of enantiomerically pure (R)- and (S)-bicalutamide

  摘要：

  The racemic antiandrogen bicalutamide is the leading antiandrogen used for the treatment of prostate cancer. The (R)-isomer possesses virtually all of the activity, but both isomers are metabolized by the liver. A convenient synthetic route to the active enantiomer would be an attractive option for patients who are hepatically impaired. We now demonstrate a rather short synthesis of (R)-bicalutamide, starting with a naturally occurring, chiral precursor. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00560-4
• 作为产物：
  描述：

  methyl 2-hydroxy-2-methyl-3-(4-fluorophenylthio)-propionate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 22.0h， 生成 2-hydroxy-2-methyl-3-(4-fluorophenylthio)-propionic acid
  参考文献：
  名称：

  Novel process for preparing and isolating rac-bicalutamide and its intermediates

  摘要：

  该发明涉及一种从乙酸乙酯和甲基丙烯酸甲酯合成外消旋和光学活性比卡鲁胺的新工艺。该发明揭示了制备比卡鲁胺中间体的过程，包括乙基-[2-{4-氟苯基砜}-2-羟基丙酸酯、1,2-环氧-2-甲基丙酸酯和2-羟基-2-甲基-3-(4-氟苯硫基)丙酸。该发明还揭示了微粉化的外消旋比卡鲁胺及其制备方法。该发明还揭示了一种新的分离和纯化外消旋和光学活性比卡鲁胺的工艺。

  公开号：

  US20040044249A1

文献信息

• Novel process for preparing and isolating rac-bicalutamide and its intermediates
  申请人：——

  公开号：US20040044249A1

  公开（公告）日：2004-03-04

  The present invention relates to a new process for the synthesis of racemic and optically active bicalutamide starting from ethyl pyruvate and methyl methacrylate. The present invention discloses processes of preparing bicalutamide intermediates including ethyl-[2-{4-fluorophenyl sulfone}]-2-hydroxy propionate, 1,2-epoxy-2-methyl propionate and 2-hydrox-2-methyl-3-(4-fluorophenylthio) propionic acid. The present invention further discloses micronized rac-bicalutamide and the preparation thereof. The present invention further discloses a new process for the isolation and purification of racemic and optically active bicalutamide.

  该发明涉及一种从乙酸乙酯和甲基丙烯酸甲酯合成外消旋和光学活性比卡鲁胺的新工艺。该发明揭示了制备比卡鲁胺中间体的过程，包括乙基-[2-4-氟苯基砜}-2-羟基丙酸酯、1,2-环氧-2-甲基丙酸酯和2-羟基-2-甲基-3-(4-氟苯硫基)丙酸。该发明还揭示了微粉化的外消旋比卡鲁胺及其制备方法。该发明还揭示了一种新的分离和纯化外消旋和光学活性比卡鲁胺的工艺。
• Syntheses of enantiomerically pure (R)- and (S)-bicalutamide
  作者：Kenneth D James、Nnochiri N Ekwuribe

  DOI：10.1016/s0040-4020(02)00560-4

  日期：2002.7

  The racemic antiandrogen bicalutamide is the leading antiandrogen used for the treatment of prostate cancer. The (R)-isomer possesses virtually all of the activity, but both isomers are metabolized by the liver. A convenient synthetic route to the active enantiomer would be an attractive option for patients who are hepatically impaired. We now demonstrate a rather short synthesis of (R)-bicalutamide, starting with a naturally occurring, chiral precursor. (C) 2002 Elsevier Science Ltd. All rights reserved.