N-Boc-(S)-[1,2-14C]valine | 318489-38-2

• 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-Boc-(S)-[1,2-14C]valine
• 英文别名: (2S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino](1,2-14C2)butanoic acid
• CAS: 318489-38-2
• 化学式: C₁₀H₁₉NO₄
• 分子量: 221.243
• InChiKey: SZXBQTSZISFIAO-JVAVPMIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-Boc-(S)-[1,2-14C]valine 、 苯甲醇 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以65%的产率得到N-Boc-(S)-[1,2-14C]valine benzyl ester
  参考文献：
  名称：

  Carbon-14 labelling of DIOVAN™ in its valine-moiety

  摘要：

  As a highly specific and non peptide AT(1)-antagonist Valsartan 2 is marketed under TM for effective treatment of hypertension. This paper the tradename DIOVAN describes the synthesis of C-14 labelled Valsartan 2, which incorporates two C-14 isotopes in the valine-moiety. Reaction of (-)-bromo-[1,2-C-14]acetyl bornane-10.2-sultam 8a ((-)-[C-14(2)]BABS) with benzophenone imine gave (-)-diphenylmethylene[1,2-C-14(2)]glycinyl bornane-10.2-sultam 9 ((-)-[C-14(2)]DPMGBS), which was alkylated with 2-iodopropane to build-up the valine structure 10. Initially the resulting sultam-protected valine 11 was treated with the benzyl bromide 12 to produce the precursor 13. However, under conditions routinely used for sultarn-cleavage deprotection resulted in the racemization of the amino acid. Successful cleavage was accomplished via N-Boc-protection of 11 followed by hydrolytic cleavage of the auxiliary and esterification to give the L-[C-14(2)]valine benzyl ester 18. Finally [C-14(2)]Valsartan 2 was synthesised in a 10 step synthesis in an overall radiochemical yield of 10 % relative to the (-)-[1,2-C-14]BABS 8a employed.

  DOI：

  10.1002/1099-1344(200011)43:13<1245::aid-jlcr412>3.0.co;2-0
• 作为产物：
  描述：

  N-Boc-(S)-[1,2-14C2]valinyl bornane-10.2 sultam 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 以100%的产率得到N-Boc-(S)-[1,2-14C]valine
  参考文献：
  名称：

  Carbon-14 labelling of DIOVAN™ in its valine-moiety

  摘要：

  As a highly specific and non peptide AT(1)-antagonist Valsartan 2 is marketed under TM for effective treatment of hypertension. This paper the tradename DIOVAN describes the synthesis of C-14 labelled Valsartan 2, which incorporates two C-14 isotopes in the valine-moiety. Reaction of (-)-bromo-[1,2-C-14]acetyl bornane-10.2-sultam 8a ((-)-[C-14(2)]BABS) with benzophenone imine gave (-)-diphenylmethylene[1,2-C-14(2)]glycinyl bornane-10.2-sultam 9 ((-)-[C-14(2)]DPMGBS), which was alkylated with 2-iodopropane to build-up the valine structure 10. Initially the resulting sultam-protected valine 11 was treated with the benzyl bromide 12 to produce the precursor 13. However, under conditions routinely used for sultarn-cleavage deprotection resulted in the racemization of the amino acid. Successful cleavage was accomplished via N-Boc-protection of 11 followed by hydrolytic cleavage of the auxiliary and esterification to give the L-[C-14(2)]valine benzyl ester 18. Finally [C-14(2)]Valsartan 2 was synthesised in a 10 step synthesis in an overall radiochemical yield of 10 % relative to the (-)-[1,2-C-14]BABS 8a employed.

  DOI：

  10.1002/1099-1344(200011)43:13<1245::aid-jlcr412>3.0.co;2-0

文献信息

• Moenius, Th.; Voges, R.; Burtscher, P., Journal of labelled compounds and radiopharmaceuticals, 1999, vol. 42, # 10, p. 1006 - 1007
  作者：Moenius, Th.、Voges, R.、Burtscher, P.、Zueger, Ch.

  DOI：——

  日期：——
• Carbon-14 labelling of DIOVAN™ in its valine-moiety
  作者：Th. Moenius、R. Voges、P. Burtscher、Ch. Züger

  DOI：10.1002/1099-1344(200011)43:13<1245::aid-jlcr412>3.0.co;2-0

  日期：2000.11

  As a highly specific and non peptide AT(1)-antagonist Valsartan 2 is marketed under TM for effective treatment of hypertension. This paper the tradename DIOVAN describes the synthesis of C-14 labelled Valsartan 2, which incorporates two C-14 isotopes in the valine-moiety. Reaction of (-)-bromo-[1,2-C-14]acetyl bornane-10.2-sultam 8a ((-)-[C-14(2)]BABS) with benzophenone imine gave (-)-diphenylmethylene[1,2-C-14(2)]glycinyl bornane-10.2-sultam 9 ((-)-[C-14(2)]DPMGBS), which was alkylated with 2-iodopropane to build-up the valine structure 10. Initially the resulting sultam-protected valine 11 was treated with the benzyl bromide 12 to produce the precursor 13. However, under conditions routinely used for sultarn-cleavage deprotection resulted in the racemization of the amino acid. Successful cleavage was accomplished via N-Boc-protection of 11 followed by hydrolytic cleavage of the auxiliary and esterification to give the L-[C-14(2)]valine benzyl ester 18. Finally [C-14(2)]Valsartan 2 was synthesised in a 10 step synthesis in an overall radiochemical yield of 10 % relative to the (-)-[1,2-C-14]BABS 8a employed.