Methyl (5S)-1-benzoyl-c-5-methyl-2-phenyl-imidazolidin-4-one-r-2-carboxylate | 134023-44-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: Methyl (5S)-1-benzoyl-c-5-methyl-2-phenyl-imidazolidin-4-one-r-2-carboxylate
• CAS: 134023-44-2
• 化学式: C₁₉H₁₈N₂O₄
• 分子量: 338.363
• InChiKey: MURAFXAZLKNHKM-ORAYPTAESA-N

反应信息

• 作为产物：
  描述：

  (S)-((S)-2-Benzoylamino-propionylamino)-phenyl-acetic acid methyl ester 在 四乙基氯化铵 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 Methyl (5S)-1-benzoyl-t-5-methyl-2-phenyl-imidazolidin-4-one-r-2-carboxylate 、 Methyl (5S)-1-benzoyl-c-5-methyl-2-phenyl-imidazolidin-4-one-r-2-carboxylate
  参考文献：
  名称：

  Anodic oxidation of N-acyl and N-alkoxycarbonyl dipeptide esters as a key step for the formation of chiral heterocyclic synthetic building blocks

  摘要：

  The anodic oxidation of N-protected dipeptide esters using chloride as a redox catalyst can be performed regioselectively at the C-terminal amino acid. With methanol as solvent, glycine as the C-terminal, and L-valine or L-proline as N-terminal amino acid methoxylation at the glycine residue takes place. Deprotection of this product leads to the (3S,6RS)-6-methoxy-2,5-piperazinedione(3) which can be applied as a chiral cationic glycine equivalent. The exchange of the methoxy group by C-nucleophiles takes place with high trans-diastereoselectivity under steric control by the substituent in 3-position. With branched amino acids at the C-terminus of the dipeptide ester the anodic oxidation in acetonitrile/methanol (95:5) as solvent with tetraethylammonium chloride as supporting electrolyte and redox catalyst leads to methyl imidazolidin-4-one-2-carboxylates. The cyclization takes place via the intermediate formation of the N-acylimino ester of the C-terminal amino acid.

  DOI：

  10.1016/s0040-4020(01)87046-0

文献信息

• Dehydrogenative cyclization of N-acyl dipeptide esters for the synthesis of imidazolidin-4-ones
  作者：Hui Yu、Jie Shen

  DOI：10.1039/c4ra15019h

  日期：——

  Dehydrogenative cyclization ofN-acyl dipeptide esters was developed and imidazolidin-4-ones were obtained in moderate to good yields by using TBHP as oxidant and KI as catalyst under mild conditions.

  以 TBHP 为氧化剂，KI 为催化剂，在温和的条件下，开发了 N-酰基二肽酯的脱氢环化反应，并以中等到良好的收率获得了咪唑烷-4-酮。