(S)-2--3-(3-tert-butyl-5-oxo-2H-isoxazol-4-yl)propionic acid | 163685-22-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (S)-2--3-(3-tert-butyl-5-oxo-2H-isoxazol-4-yl)propionic acid
• 英文别名: (2S)-3-(3-tert-butyl-5-oxo-2H-1,2-oxazol-4-yl)-2-[(9-phenylfluoren-9-yl)amino]propanoic acid
• CAS: 163685-22-1
• 化学式: C₂₉H₂₈N₂O₄
• 分子量: 468.552
• InChiKey: OGHJVNQNDOESNZ-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-2--3-(3-tert-butyl-5-oxo-2H-isoxazol-4-yl)propionic acid 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 以88%的产率得到(S)-2-Amino-3-(3-tert-butyl-5-oxo-2H-isoxazol-4-yl)propionic acid
  参考文献：
  名称：

  Synthesis of (S)-2-Amino-3-(3-tert-butyl-5-oxo-2H-isoxazol-4-yl)propionic Acid

  摘要：

  An efficient method for synthesizing enantiopure isoxazole amino acids has been developed. (2S)-2-Amino-3-(3-tert-tert-butyl-5-oxo-2H-isoxazol-4-yl) propionic acid (1) was synthesized in three steps from L-gamma-methyl N-(9-(9-phenylfluorenyl))glutamate (2) in 46% overall yield. Acylation of the dianion of 2 with pivaloyl chloride provides beta-keto ester 3 in 75% yield after chromatography. (2S)-2-[N-(9-(9-phenylfluorenyl))amino]-3 -(3-tert-butyl-5-oxo-2H-isoxazol-4-yl)propionic acid (4) was isolated as a white crystalline solid from the reaction of 3 with hydroxylamine under basic conditions followed by exposure to HCl. The crystal structure of 4 confirmed the presence of a 3-tert-butyl-4-isoxazol-5(2H)-one. Title compound 1 was obtained by removal of the PhFl protecting group of 4 using either trifluoroacetic acid in CH2Cl2 or lithium in liquid ammonia. Alkylation of 4 with iodomethane provided a mixture containing (2S,4S)-methyl 2-[N-(9-(9-phenylfluorenyl))amino]-3-(3 -tert-butyl-4-methyl-5-oxo-4H-isoxazol-4-yl)propionate (5) and (2S)-methyl 2-[N-(9-(9-phenylfluorenyl))amino]-3-(2-methyl-3-tert-butyl-5-oxo-2H-isoxazol-4-yl)propionate (6). Single crystal X-ray analyses of the structures of 4-6 provide insight into the mechanism of alkylation as well as the configurational stability of N-(9-(9-phenylfluorenyl))amino carbonyl compounds.

  DOI：

  10.1021/jo00115a039
• 作为产物：
  描述：

  (2S,4RS)-6,6-dimethyl-5-oxo-4-<(methyloxy)carbonyl>-2-heptanoic acid 在 sodium hydroxide 、 盐酸羟胺 作用下， 以 甲醇 为溶剂， 反应 1.67h， 以69%的产率得到(S)-2--3-(3-tert-butyl-5-oxo-2H-isoxazol-4-yl)propionic acid
  参考文献：
  名称：

  Synthesis of (S)-2-Amino-3-(3-tert-butyl-5-oxo-2H-isoxazol-4-yl)propionic Acid

  摘要：

  An efficient method for synthesizing enantiopure isoxazole amino acids has been developed. (2S)-2-Amino-3-(3-tert-tert-butyl-5-oxo-2H-isoxazol-4-yl) propionic acid (1) was synthesized in three steps from L-gamma-methyl N-(9-(9-phenylfluorenyl))glutamate (2) in 46% overall yield. Acylation of the dianion of 2 with pivaloyl chloride provides beta-keto ester 3 in 75% yield after chromatography. (2S)-2-[N-(9-(9-phenylfluorenyl))amino]-3 -(3-tert-butyl-5-oxo-2H-isoxazol-4-yl)propionic acid (4) was isolated as a white crystalline solid from the reaction of 3 with hydroxylamine under basic conditions followed by exposure to HCl. The crystal structure of 4 confirmed the presence of a 3-tert-butyl-4-isoxazol-5(2H)-one. Title compound 1 was obtained by removal of the PhFl protecting group of 4 using either trifluoroacetic acid in CH2Cl2 or lithium in liquid ammonia. Alkylation of 4 with iodomethane provided a mixture containing (2S,4S)-methyl 2-[N-(9-(9-phenylfluorenyl))amino]-3-(3 -tert-butyl-4-methyl-5-oxo-4H-isoxazol-4-yl)propionate (5) and (2S)-methyl 2-[N-(9-(9-phenylfluorenyl))amino]-3-(2-methyl-3-tert-butyl-5-oxo-2H-isoxazol-4-yl)propionate (6). Single crystal X-ray analyses of the structures of 4-6 provide insight into the mechanism of alkylation as well as the configurational stability of N-(9-(9-phenylfluorenyl))amino carbonyl compounds.

  DOI：

  10.1021/jo00115a039

文献信息

• Synthesis of (S)-2-Amino-3-(3-tert-butyl-5-oxo-2H-isoxazol-4-yl)propionic Acid
  作者：Mohamed Atfani、William D. Lubell

  DOI：10.1021/jo00115a039

  日期：1995.5

  An efficient method for synthesizing enantiopure isoxazole amino acids has been developed. (2S)-2-Amino-3-(3-tert-tert-butyl-5-oxo-2H-isoxazol-4-yl) propionic acid (1) was synthesized in three steps from L-gamma-methyl N-(9-(9-phenylfluorenyl))glutamate (2) in 46% overall yield. Acylation of the dianion of 2 with pivaloyl chloride provides beta-keto ester 3 in 75% yield after chromatography. (2S)-2-[N-(9-(9-phenylfluorenyl))amino]-3 -(3-tert-butyl-5-oxo-2H-isoxazol-4-yl)propionic acid (4) was isolated as a white crystalline solid from the reaction of 3 with hydroxylamine under basic conditions followed by exposure to HCl. The crystal structure of 4 confirmed the presence of a 3-tert-butyl-4-isoxazol-5(2H)-one. Title compound 1 was obtained by removal of the PhFl protecting group of 4 using either trifluoroacetic acid in CH2Cl2 or lithium in liquid ammonia. Alkylation of 4 with iodomethane provided a mixture containing (2S,4S)-methyl 2-[N-(9-(9-phenylfluorenyl))amino]-3-(3 -tert-butyl-4-methyl-5-oxo-4H-isoxazol-4-yl)propionate (5) and (2S)-methyl 2-[N-(9-(9-phenylfluorenyl))amino]-3-(2-methyl-3-tert-butyl-5-oxo-2H-isoxazol-4-yl)propionate (6). Single crystal X-ray analyses of the structures of 4-6 provide insight into the mechanism of alkylation as well as the configurational stability of N-(9-(9-phenylfluorenyl))amino carbonyl compounds.