methyl (S)-5-[α-(tert-butoxycarbonylamino)phenethyl]-oxazole-4-carboxylate | 81327-39-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (S)-5-[α-(tert-butoxycarbonylamino)phenethyl]-oxazole-4-carboxylate
• 英文别名: methyl (S)-5-[1-(tert-butoxycarbonylamino)-2-phenylethyl]oxazole-4-carboxylate；(s)-5-(1-Tert-butoxycarbonylamino-2-phenylethyl)oxazole-4-carboxylic acid methyl ester；methyl 5-[(1S)-1-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylethyl]-1,3-oxazole-4-carboxylate
• CAS: 81327-39-1
• 化学式: C₁₈H₂₂N₂O₅
• 分子量: 346.383
• InChiKey: IYUCGGPSRZIGJP-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  90.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (S)-5-[α-(tert-butoxycarbonylamino)phenethyl]-oxazole-4-carboxylate 在 三氟乙酸 作用下， 反应 1.0h， 生成 methyl (S)-5-(α-aminophenethyl)oxazole-4-carboxylate Trifluoroacetate
  参考文献：
  名称：

  Bicyclic pyrrolyl amides as glucogen phosphorylase inhibitors

  摘要：

  杂环酰胺衍生物的化学式（I）：其中—X-Y-Z-选择自—S—CR4═CR5—，—CR4═CR5—S—，—O—CR4═CR5—，—CR4═CR5—O—，—N═CR4—S—，—S—CR4═N—，—NR6—CR4═CR5—和—CR4═CR5—NR6—；或其药学上可接受的盐或体内可水解酯；（附带条件）；具有糖原磷酸化酶抑制活性，因此在治疗与糖原磷酸化酶活性增加相关的疾病状态中具有价值。描述了制备所述杂环酰胺衍生物和含有它们的药物组合物的方法。

  公开号：

  US20030232875A1
• 作为产物：
  描述：

  BOC-L-苯丙氨酸 、 异腈基乙酸甲酯 在 叠氮磷酸二苯酯 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以70%的产率得到methyl (S)-5-[α-(tert-butoxycarbonylamino)phenethyl]-oxazole-4-carboxylate
  参考文献：
  名称：

  有机合成的新方法和试剂22，叠氮基磷酸二苯酯1，用于异氰酸酯甲酯与羧酸的c-酰化反应的试剂

  摘要：

  叠氮基磷酸二苯酯（DPPA）可有效用于异氰基乙酸甲酯与羧酸的直接C-酰化反应，得到4-甲氧基羰基恶唑。

  DOI：

  10.1016/s0040-4039(00)86794-5

文献信息

• [EN] INDOLE-AMID DERIVATIVES WHICH POSSESS GLYCOGEN PHOSPHORYLASE INHIBITORY ACTIVITY<br/>[FR] DERIVES D'AMIDO-INDOLE POSSEDANT UNE ACTIVITE D'INHIBITION DE LA GLYCOGENE PHOSPHORYLASE
  申请人：ASTRAZENECA AB

  公开号：WO2003074517A1

  公开（公告）日：2003-09-12

  Heterocyclic amides of formula (1), wherein: m is 0, 1 or 2; n is 0, 1 or 2; B is phenyl or heterocyclyl; R1 is selected from for example halo, nitro, cyano, hydroxy, carboxy; R2 and R3 are independently selected from, for example, C5-7cycloalkyl, cyano(C1-4)alkyl, C1-4alkyl (optionally substituted with 1 or 2 R8 groups), -OR8 and R8; R4 is independently selected from for example hydrogen, halo, nitro, cyano, hydroxy, C1-4alkyl, and C1-4alkanoyl; R8 is selected from for example hydroxy, heterocyclyl, aryl, -COCOOR9, -C(O)N(R9)(R10), (R9)(R10)N- and -COOR9; R9 and R10 are selected from for example hydrogen, hydroxy, C1-4alkyl (optionally substituted by 1 or 2 R13); R13 is selected from for example, hydroxy, C1-4alkoxy, heterocyclyl and C1-4alkanoyl; R14 is selected from for example, hydrogen, halo, C1-4alkyl, C5-7cycloalkyl, C1-4alkoxy, cyano, cyano(C1-4)alkyl, -COR3, (R2)(R3)NCO-, and (R2)(R3)NSO2-; or a pharmaceutically acceptable salt or pro-drug thereof; possess glycogen phosphorylase inhibitory activity and accordingly have value in the treatment of disease states associated with increased glycogen phosphorylase activity. Processes for the manufacture of said heterocyclic amide derivatives and pharmaceutical compositions containing them are described.

  公式（1）中的杂环酰胺，其中：m为0、1或2；n为0、1或2；B为苯基或杂环基；R1从卤、硝基、氰基、羟基、羧基等中选择；R2和R3分别从C5-7环烷基、氰基（C1-4）烷基、C1-4烷基（可选地取代1或2个R8基）、-OR8和R8中选择；R4从氢、卤、硝基、氰基、羟基、C1-4烷基和C1-4烷酰基等中选择；R8从羟基、杂环基、芳基、-COCOOR9、-C（O）N（R9）（R10）、（R9）（R10）N-和-COOR9等中选择；R9和R10从氢、羟基、C1-4烷基（可选地取代1或2个R13）中选择；R13从羟基、C1-4烷氧基、杂环基和C1-4烷酰基等中选择；R14从氢、卤、C1-4烷基、C5-7环烷基、C1-4烷氧基、氰基、氰基（C1-4）烷基、-COR3、（R2）（R3）NCO-和（R2）（R3）NSO2-等中选择；或其药学上可接受的盐或前药；具有糖原磷酸化酶抑制活性，因此在治疗与糖原磷酸化酶活性增加有关的疾病状态方面具有价值。描述了制造该杂环酰胺衍生物和含有它们的制药组合物的过程。
• Indole-amid derivatives which possess glycogen phosphorylase inhibitory activity
  申请人：Stocker Andrew

  公开号：US20050130963A1

  公开（公告）日：2005-06-16

  Heterocyclic amides of formula (1) wherein: m is 0, 1 or 2; n is 0, 1 or 2; B is phenyl or heterocyclyl; R 1 is selected from for example halo, nitro, cyano, hydroxy, carboxy; R 2 and R 3 are independently selected from, for example, C 5-7 cycloalkyl, cyano(C 1-4 )alkyl, C 1-4 alkyl (optionally substituted with 1 or 2 R 8 groups), OR 8 and R 8 ; R 4 is independently selected from for example hydrogen, halo, nitro, cyano, hydroxy, C 1-4 alkyl, and C 1-4 alkanoyl; R 8 is selected from for example hydroxy, heterocyclyl, aryl, —COCOOR 9 , —C(O)N(R 9 )(R 10 ), (R 9 )(R 10 )N— and —COOR 9 ; R 9 and R 10 are selected from for example hydrogen, hydroxy, C 1-4 alkyl (optionally substituted by 1 or 2 R 13 ); R 13 is selected from for example, hydroxy, C 1-4 alkoxy, heterocyclyl and C 1-4 alkanoyl; R 14 is selected from for example, hydrogen, halo, C 1-4 alkyl, C 5-7 cycloalkyl, C 1-4 alkoxy, cyano, cyano(C 1-4 )alkyl, —COR 3 , (R 2 )(R 3 )NCO—, and (R 2 )(R 3 )NSO 2 —; or a pharmaceutically acceptable salt or pro-drug thereof; possess glycogen phosphorylase inhibitory activity and accordingly have value in the treatment of disease states associated with increased glycogen phosphorylase activity. Processes for the manufacture of said heterocyclic amide derivatives and pharmaceutical compositions containing them are described.

  式（1）中的杂环酰胺，其中：m为0、1或2；n为0、1或2；B为苯基或杂环基；R1从卤素、硝基、氰基、羟基、羧基等中选择；R2和R3分别从C5-7环烷基、氰基（C1-4）烷基、C1-4烷基（可选地取代1或2个R8基）、OR8和R8中独立选择；R4从氢、卤素、硝基、氰基、羟基、C1-4烷基和C1-4烷酰基等中独立选择；R8从羟基、杂环基、芳基、—COCOOR9、—C（O）N（R9）（R10）、（R9）（R10）N—和—COOR9等中选择；R9和R10从氢、羟基、C1-4烷基（可选地取代1或2个R13）等中选择；R13从羟基、C1-4烷氧基、杂环基和C1-4烷酰基等中选择；R14从氢、卤素、C1-4烷基、C5-7环烷基、C1-4烷氧基、氰基、氰基（C1-4）烷基、—COR3、（R2）（R3）NCO—和（R2）（R3）NSO2—等中选择；或其药学上可接受的盐或前药。这些化合物具有糖原磷酸化酶抑制活性，因此在治疗与糖原磷酸化酶活性增加相关的疾病状态方面具有价值。描述了制备上述杂环酰胺衍生物的方法和含有它们的制药组合物。
• Bicyclic pyrrolyl amides as glucogen phosphorylase inhibitors
  申请人：——

  公开号：US20030232875A1

  公开（公告）日：2003-12-18

  Heterocyclic amide derivatives, of formula (I): wherein —X-Y-Z- is selected from —S—CR 4 ═CR 5 —, —CR 4 ═CR 5 —S—, —O—CR 4 ═CR 5 —, —CR 4 ═CR 5 —O—, —N═CR 4 —S—, —S—CR 4 ═N—, —NR 6 —CR 4 ═CR 5 — and —CR 4 ═CR 5 —NR 6 —; or a pharmaceutically acceptable salt or an in vivo hydrolysable ester thereof; (with provisos); possess glycogen phosphorylase inhibitory activity and accordingly have value in the treatment of disease states associated with increased glycogen phosphorylase activity. Processes for the manufacture of said heterocyclic amide derivatives and pharmaceutical compositions containing them are described.

  杂环酰胺衍生物的化学式（I）：其中—X-Y-Z-选择自—S—CR4═CR5—，—CR4═CR5—S—，—O—CR4═CR5—，—CR4═CR5—O—，—N═CR4—S—，—S—CR4═N—，—NR6—CR4═CR5—和—CR4═CR5—NR6—；或其药学上可接受的盐或体内可水解酯；（附带条件）；具有糖原磷酸化酶抑制活性，因此在治疗与糖原磷酸化酶活性增加相关的疾病状态中具有价值。描述了制备所述杂环酰胺衍生物和含有它们的药物组合物的方法。
• New methods and reagents in organic synthesis, 22,1 diphenyl phosphorazidate as a reagent for c-acylation of methyl isocyanoacetate with carboxylic acids
  作者：Yasumasa Hamada、Takayuki Shioiri

  DOI：10.1016/s0040-4039(00)86794-5

  日期：1982.1

  Diphenyl phosphorazidate (DPPA) can be used efficiently for the direct C-acylation of methyl isocyanoacetate with carboxylic acids, giving 4-methoxycarbonyloxazoles.

  叠氮基磷酸二苯酯（DPPA）可有效用于异氰基乙酸甲酯与羧酸的直接C-酰化反应，得到4-甲氧基羰基恶唑。