5-benzoylamino-6-oxo-2-phenyl-1(6H)-pyrimidineacetic acid tert-butyl ester | 634148-47-3

• 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: 5-benzoylamino-6-oxo-2-phenyl-1(6H)-pyrimidineacetic acid tert-butyl ester
• 英文别名: 1-(tert-butoxycarbonylmethyl)-6-oxo-2-phenyl-5-benzoylamino-1,6-dihydropyrimidine；tert-butyl 2-(5-benzamido-6-oxo-2-phenylpyrimidin-1-yl)acetate
• CAS: 634148-47-3
• 化学式: C₂₃H₂₃N₃O₄
• 分子量: 405.453
• InChiKey: DWLBWFWXQWKXIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  88.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-benzoylamino-6-oxo-2-phenyl-1(6H)-pyrimidineacetic acid tert-butyl ester 在 甲醇 、 sodium hydroxide 、 水 、 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 生成 5-氨基-6-氧代-2-苯基-1(6h)-嘧啶乙酸
  参考文献：
  名称：

  EP1553090

  摘要：

  公开号：
• 作为产物：
  描述：

  N-(tert-butoxycarbonylmethyl)benzamidine hydrochloride 在 sodium carbonate 作用下， 以 水 、 甲苯 、 乙腈 为溶剂， 反应 17.0h， 生成 5-benzoylamino-6-oxo-2-phenyl-1(6H)-pyrimidineacetic acid tert-butyl ester
  参考文献：
  名称：

  Syntheses of 5-Amino-2-phenyl-4(3H)-pyrimidinone Derivatives Starting with Glycine

  摘要：

  N-Cbz derivative of 5-amino-2-phenyl-4(3H)-pyrimidinone was prepared from sodium salt of methyl hydroxymethylene glycinate and benzamidine hydrochloride in good yield. However, the reaction with N-substituted benzamidine did not proceed to give the desired pyrimidinone. In contrast, the reaction of 4-ethoxymethylene-2-phenyl-5(4H)-oxazolone readily prepared from hippuric acid and N-substituted benzamidine proceeded nicely to give 5-(benzoylamino)-6-oxo-2-phenyl-1(6H)-pyrimidineacetic acid in high yield.

  DOI：

  10.3987/com-12-12432

文献信息

• Process for preparing pyrimidine compound
  申请人：Takahashi Daisuke

  公开号：US20050165234A1

  公开（公告）日：2005-07-28

  Azlactone Compound (2) is reacted with Amidine Compound (3) to give Pyrimidine Compound (1) which is useful as an intermediate for the production of enzyme inhibitors (e.g., elastase inhibitor, chymase inhibitor etc.): wherein each symbol is as defined in the specification.

  Azlactone化合物(2)与Amidine化合物(3)反应，得到嘧啶化合物(1)，该化合物可用作生产酶抑制剂（例如弹性蛋白酶抑制剂，胰蛋白酶抑制剂等）的中间体：其中每个符号如规范所定义。
• PROCESS FOR PRODUCING PYRIMIDINE COMPOUND
  申请人：Ajinomoto Co., Inc.

  公开号：EP1553090A1

  公开（公告）日：2005-07-13

  Azlactone Compound (2) is reacted with Amidine Compound (3) to give Pyrimidine Compound (1) useful as an intermediate for enzyme inhibitors (e.g., elastase inhibitor, chymase inhibitor etc.): Pyrimidine Compound (1) Azlactone Compound (2) Amidine Compound (3) wherein each symbol is as defined in the specification.

  氮内酯化合物（2）与脒化合物（3）反应生成嘧啶化合物（1），可用作酶抑制剂 （如弹性蛋白酶抑制剂、糜蛋白酶抑制剂等）的中间体： 嘧啶化合物(1) 阿兹内酯化合物(2) 脒化合物(3) 其中各符号如说明书中所定义。
• An Improved Synthesis of 5-Acylamino-6-oxo-2-phenyl-1(6H)-pyrimidineacetic Acid from Glycine with Readily Removable Protecting Groups
  作者：Daisuke Takahashi、Kunisuke Izawa、Tatsumi Kashiwagi、Hiromi Onoye、Robert M. Williams

  DOI：10.3987/com-12-12518

  日期：——

  Concise synthesis of N-acyl-5-amino-6-oxo-2-phenyl-1(6H)-yrimidineacetic acid was achieved by cyclization reaction of 2-alkyl-4-lkoxymethylene-5(4H)-oxazolone with N-(carboxymethyl)benzamidine, while a similar reaction with sodium salt of 2-alkyl-4-hydroxymethylene-5(4H)-xazolones gave a mixture of regioisomers of the pyrimidinone. N-Acyl groups (acetyl or phenylacetyl) of the pyrimidinone derivatives were readily cleaved under very mild conditions with weak base or enzyme. Thus, the process enabled us to synthesize the drug candidate without exchanging N-protecting group. Since the starting oxazolones were easily prepared from N-acylglycine, the synthetic route can be used for the large scale synthesis of the key intermediate for several enzyme inhibitors.