N-(2-diazo-3-oxobutanoyl)-N-(phenylmethyl)-L-phenylalanine ethyl ester | 168336-17-2

• 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: N-(2-diazo-3-oxobutanoyl)-N-(phenylmethyl)-L-phenylalanine ethyl ester
• CAS: 168336-17-2
• 化学式: C₂₂H₂₃N₃O₄
• 分子量: 393.442
• InChiKey: OZDJSVHVYPKEAZ-IBGZPJMESA-N

反应信息

• 作为反应物：
  描述：

  N-(2-diazo-3-oxobutanoyl)-N-(phenylmethyl)-L-phenylalanine ethyl ester 在 rhodium(II) acetate dimer 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 10.0h， 以23%的产率得到(3R,4S)-3-acetyl-1-<(1S)-1-ethoxycarbonyl-2-phenylethyl>-4-phenylazetidin-2-one
  参考文献：
  名称：

  Rhodium(II) acetate-catalysed decomposition of 2-diazo-3-oxobutanamides derived from L-phenylalanine

  摘要：

  In order to developed a practical method for alkylating alpha-amino acids at the alpha- or beta-carbon atom by intramolecular carbene C-H insertion, a series of diazoamides 3a-e was synthesized and subjected to rhodium(II) acetate-catalysed decomposition. The N-benzyl derivative 3a gave mainly the azetidinones 4a and 5a, resulting from a carbene C-H insertion into the N-benzyl group. The N-diphenylmethyl derivative 3c yielded, upon treatment with rhodium(II) acetate, the azetidinone 5c, the imine 6c, the cycloheptapyrrolidinone 7c as well as the desired pyrrolidinone 8c (22% yield) the latter resulting from an alkylation of the L-phenylalanine framework at the beta-carbon atom.

  DOI：

  10.1002/prac.19953370160
• 作为产物：
  描述：

  N-(3-oxobutanoyl)-N-(phenylmethyl)-L-phenylalanine ethyl ester 在 2-azido-1-ethylpyridin-1-ium tetrafluoroborate 作用下， 以80%的产率得到N-(2-diazo-3-oxobutanoyl)-N-(phenylmethyl)-L-phenylalanine ethyl ester
  参考文献：
  名称：

  Rhodium(II) acetate-catalysed decomposition of 2-diazo-3-oxobutanamides derived from L-phenylalanine

  摘要：

  In order to developed a practical method for alkylating alpha-amino acids at the alpha- or beta-carbon atom by intramolecular carbene C-H insertion, a series of diazoamides 3a-e was synthesized and subjected to rhodium(II) acetate-catalysed decomposition. The N-benzyl derivative 3a gave mainly the azetidinones 4a and 5a, resulting from a carbene C-H insertion into the N-benzyl group. The N-diphenylmethyl derivative 3c yielded, upon treatment with rhodium(II) acetate, the azetidinone 5c, the imine 6c, the cycloheptapyrrolidinone 7c as well as the desired pyrrolidinone 8c (22% yield) the latter resulting from an alkylation of the L-phenylalanine framework at the beta-carbon atom.

  DOI：

  10.1002/prac.19953370160