引用本文:
王亚楼, 刘星, 李江川. 2-(5-甲基-2-苯基-4-噁唑基)乙醇的合成[J]. 应用化学,
2004, 21(1): 104-106.
Citation: WANG Ya-Lou, LIU Xing, LI Jiang-Chuan. Synthesis of 2-(5-Methyl-2-phenyl-4-oxazolyl)ethanol[J]. Chinese Journal of Applied Chemistry, 2004, 21(1): 104-106.
Citation: WANG Ya-Lou, LIU Xing, LI Jiang-Chuan. Synthesis of 2-(5-Methyl-2-phenyl-4-oxazolyl)ethanol[J]. Chinese Journal of Applied Chemistry, 2004, 21(1): 104-106.
2-(5-甲基-2-苯基-4-噁唑基)乙醇的合成
摘要:
胰岛素抵抗改善剂已经成为Ⅱ型糖尿病治疗药物研究开发的一个热点,这类药物的作用机制一般认为是激活PPARγ受体[1],已经上市的吡格列酮和罗格列酮由于它们对Ⅱ型糖尿病人的胰岛素抵抗改善明显,市场前景十分广阔。
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关键词:
- 甲基苯基噁唑)乙醇
- / Dakin-West反应
- / LiAlH4还原
- / 合成
English
Synthesis of 2-(5-Methyl-2-phenyl-4-oxazolyl)ethanol
Abstract:
2-(5-Methyl-2-phenyl-4-oxazolyl)ethanol(1) was synthesized from L-aspartic acid via 5-step reactions; esterification, N-benzoylation, Dakin-West reaction, cyclizaction and reduction using LiAlH4 in about 31.2% overall yield. Reacting L-aspartic acid with methanol in 0℃ gave 72.6% L-aspartic acid β-methyl ester hydrochloride(2), which was benzoylated to give 82.0% N-benzoyl-L-aspartic acid β-methyl ester(3). Dakin-West reaction of 3 gave 74.4% methyl 3-benzamido-4-oxovalerate(4), which was cyclized in toluene by POCl3 to give 81.8% methyl 2-(5-methyl-2-phenyl-4-oxazolyl)acetate(5), the latter can easily convert to 1 by treatment with ether solution of LiAlH4 in yield of 86%. All the compounds were characterized by 1H NMR, IR and elemental analysis.
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Key words:
- (methyl-phenyl-oxazolyl)ethanol
- / Dakin-West reaction
- / reduction
- / synthesis
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