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,C13H23NO3,241.3332,isopropyl N-[(1S)-2-cyclohexyl-1-formyle

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摘 要:,C13H23NO3,241.3332,isopropyl N-[(1S)-2-cyclohexyl-1-formylethyl]carbamate
  • 【化学名】isopropyl N-[(1S)-2-cyclohexyl-1-formylethyl]carbamate
  • 【CAS登记号】
  • 【结构式】,C13H23NO3,241.3332,isopropyl N-[(1S)-2-cyclohexyl-1-formyle--药物合成数据库
  • 【分子式】C13H23NO3
  • 【分子量】241.3332
  • 【来源】
  • 【合成情况】 
  • 〖目标产物〗KRI-1314
  • 〖合成路线〗
  • 〖合成方法〗2) Synthesis of (2R,3S)-3-amino-4-cyclohexyl-2-hydroxybutyric acid isopropyl ester (II): Phenylalanine methyl ester (XIII) is protected with isopropyl chloroformate and triethylamine in THF to give N-(isopropoxycarbonyl)phenylalanine methyl ester (XIV), which is reduced with NaBH4 - LiCl in THF - ethanol, yielding N-(isopropoxycarbonyl)phenylalaninol (XV). The hydrogenation of (XV) with H2 over Rh/Al2O3 in methanol affords N-(isopropoxycarbonyl)cyclohexylalaninol (XVI), which is oxidized with pyridine - SO3 in DMSO to the corresponding aldehyde (XVII). The reaction of (XVII) with NaCN - HCl in CHCl3 - water affords (2R,3S)-3-amino-4-cyclohexyl-2-hydroxybutyric acid (XVIII), which is finally esterified with isopropanol - HCl to give (II). 3) Synthesis of KRY-1314: By condensation of N(tau)-tert-butoxycarbonyl-N(alpha)-[2(R)-(morpholinocarbonylmethyl)-3-(1-naphthyl)propionyl]histidine (I) with (2R,3S)-3-amino-4-cyclohexyl-2-hydroxybutyric acid isopropyl ester (II) by means of dicyclohexylcarbodiimide (DCC) and N-hydroxy-5-norbornene-2,3-dicarboximide (HONB) in acetonitrile - triethylamine.
  • 〖参考〗Harada, H.; Iyobe, A.; Tsubaki, A.; Yamaguchi, T.; Kamijo, T.; Kiso, Y.; Iizuka, K.; Hirata, K.; A practical synthesis of an orally potent renin inhibitor, isopropyl (2R,3S)-4-cyclohexyl-2-hydroxy-3-[N-[(2R)-2-morpholinocarbonylmethyl-3-(1-naaphthyl)propi i?ab??电?h扰h?a?缟h?aIS/STR/1233/
 
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