Carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester 4-methoxy-benzyl ester | 30761-97-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester 4-methoxy-benzyl ester
• 英文别名: 1-({[(4-Methoxyphenyl)methoxy]carbonyl}oxy)pyrrolidine-2,5-dione；(2,5-dioxopyrrolidin-1-yl) (4-methoxyphenyl)methyl carbonate
• CAS: 30761-97-8
• 化学式: C₁₃H₁₃NO₆
• 分子量: 279.249
• InChiKey: RUPVJXBCXCVMAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R)-2-amino-3-[3,4-bis(phenylmethoxy)phenyl]-3-hydroxypropanoic acid;hydrochloride 、 Carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester 4-methoxy-benzyl ester 生成 (3R)-3-[3,4-bis(phenylmethoxy)phenyl]-3-hydroxy-2-[(4-methoxyphenyl)methoxycarbonylamino]propanoic acid
  参考文献：
  名称：

  UMEZAWA, HAMAO;NAGATSU, TOSHIHARU;NARABAYASHI, HIROTARO;TAKEUCHI, TOMIO;I+

  摘要：

  DOI：

文献信息

• Threo-adrenalinecarboxylic acid, processes for the production thereof, and pharmaceutical compositions thereof
  申请人：ZAIDAN HOJIN BISEIBUTSU KAGAKU KENKYU KAI

  公开号：EP0112606A1

  公开（公告）日：1984-07-04

  DL- and L-Threo-3-(3,4-dihydroxyphenyl)-N-methyl-serine which may also be termed as DL- and L-threo-adrenalinecarboxylic acid are now provided, which are new compounds useful for therapeutic treatment of Parkinson's disease and mental depression disease. DL-Adrenalinecarboxylic acid may be produced by a new process comprising reacting glycine with O-protected 3,4-dihydroxybenzaldehyde, hydrolyzing the resultant reaction product under acidic conditions to form O-protected DL-3-(3,4-dihydroxyphenyl)serine, isolating the O-protected DL-3-(3,4-dihydroxyphenyl)serine into the threo isomer and the erythro isomer by recrystallization from a suitable organic solvent, introducing an unsubstituted or substituted benzyl group into the 2-amino group of the resulting O-protected DL-threo-3-(3,4-dihydroxyphenyl)serine, then N-methylating the resulting O-protected DL-threo-3-(3,4-dihydroxyphenyl)-N-benzylserine,and removing the O-protecting groups as well as the unsubstituted or substituted benzyl group at the 2-methylamino group of the N-methylation product. L-threo-Adrenalinecarboxylic acid may be produced by a new process comprising introducing a p-methoxybenzyloxycarbonyl group into the 2-amino group of the O-protected DL-threo-3-(3,4-dihydroxyphenyl)serine obtained as an intermediate product, optically resolving the resultant 0-protected DL-threo-3-(3,4-dihydroxyphenyl)-N-p-methoxybenzyloxycarbonyl-serine by reacting the latter with an optically active amine and recrystallizing the resultant amine salt products from a suitable organic solvent, removing the p-methoxybenzyloxycarbonyl group from the resultant O-protected L-threo-(3,4-dihydroxyphenyl)-N-p-methoxybenzyloxycarbonyl-serine, reacting the resultant O-protected L-threo-(3,4-dihydroxyphenyl)serine with dimethyl sulfate in dry acetone to form an O-protected L-threo-(3,4-dihydroxyphenyl)-N-methylserine methyl ester, saponifying this methyl ester and then removing the O-protecting groups from the saponification product.

  现在提供的 DL-和 L-苏-3-(3,4-二羟基苯基)-N-甲基丝氨酸也可称为 DL-和 L-苏-肾上腺素羧酸，它们是可用于治疗帕金森病和精神抑郁症的新化合物。DL-肾上腺素羧酸可通过一种新工艺生产，该工艺包括使甘氨酸与 O-保护的 3,4-二羟基苯甲醛反应，在酸性条件下水解反应产物，形成 O-保护的 DL-3-(3,4-二羟基苯基)丝氨酸，通过从合适的有机溶剂中重结晶，将 O-保护的 DL-3-(3,4-二羟基苯基)丝氨酸分离成苏氨酸异构体和赤藓醇异构体、将未取代或取代的苄基引入到所得 O-保护的 DL-苏-3-(3,4-二羟基苯基)丝氨酸的 2-氨基中，然后将所得 O-保护的 DL-苏-3-(3,4-二羟基苯基)-N-苄丝氨酸 N-甲基化，并去除 O-保护基团以及 N-甲基化产物的 2-甲基氨基上的未取代或取代的苄基。 L-硫代肾上腺素羧酸可通过一种新工艺生产，该工艺包括在作为中间产物获得的 O-保护基 DL-硫代-3-(3,4-二羟基苯基)丝氨酸的 2-氨基上引入对甲氧基苄氧羰基、通过使 0-保护的 DL-苏氨酰-3-(3,4-二羟基苯基)-N-对甲氧基苄氧羰基丝氨酸与光学活性胺反应，并从合适的有机溶剂中重结晶所得到的胺盐产物，从而对 0-保护的 DL-苏氨酰-3-(3,4-二羟基苯基)-N-对甲氧基苄氧羰基丝氨酸进行光学解析、从得到的 O-保护的 L-硫代-(3,4-二羟基苯基)-N-对甲氧基苄氧羰基丝氨酸中除去对甲氧基苄氧羰基，将得到的 O-保护的 L-硫代-(3、在干丙酮中与硫酸二甲酯反应，形成 O-保护的 L-硫代-(3,4-二羟基苯基)-N-甲基丝氨酸甲酯，将该甲酯皂化，然后从皂化产物中去除 O-保护基团。
• 1-PHENYL-SUBSTITUTED HETEROCYCLYL DERIVATIVES AND THEIR USE AS PROSTAGLANDIN D2 RECEPTOR MODULATORS
  申请人：Actelion Pharmaceuticals Ltd.

  公开号：EP2590944B1

  公开（公告）日：2015-09-30
• US4833268A
  申请人：——

  公开号：US4833268A

  公开（公告）日：1989-05-23