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Diamino acid derivative starting material, manufacturing method thereof, and diamino acid derivative manufacturing method

Foreign code F110003954
File No. E07616WO
Posted date Jul 7, 2011
Country EPO
Application number 09720699
Gazette No. 2269979
Gazette No. 2269979
Date of filing Feb 27, 2009
Gazette Date Jan 5, 2011
Gazette Date Apr 16, 2014
International application number JP2009053681
International publication number WO2009113409
Date of international filing Feb 27, 2009
Date of international publication Sep 17, 2009
Priority data
  • 2009JP053681 (Feb 27, 2009) WO
  • P2008-058993 (Mar 10, 2008) JP
Title Diamino acid derivative starting material, manufacturing method thereof, and diamino acid derivative manufacturing method
Abstract Provided is an efficient technology for synthesizing diamino acids (diamino acid derivatives).
Disclosed is a manufacturing method for diamino acid derivatives wherein the fluorenyl groups of the diamino acid derivative starting materials represented by General Formula [II] or [IV] are removed.
Scope of claims [claim1]
1. A manufacturing method of starting materials of diamino acid derivatives represented by the following general formula [II], wherein (see diagramm) R **2, is a substituted hydrocarbon group or an unsubstituted hydrocarbon group and all of R **2 may be identical to each other, or may differ from each other; R **3 is a substituted hydrocarbon group, a substituted heterocyclic group, an unsubstituted hydrocarbon group, or an unsubstituted heterocyclic group; R **4 is an electron-withdrawing group and the fluorenyl group is a ring-substituted fluorenyl group or a ring-unsubstituted fluorenyl group;
said manufacturing method comprising reacting a compound represented by the following general formula [I], wherein (see diagramm) R **2 is a substituted hydrocarbon group or an unsubstituted hydrocarbon group and all of R **2 may be identical to each other, or may differ from each other and the fluorenyl group is a ring-substituted fluorenyl group or a ring-unsubstituted fluorenyl group;
with a compound represented by the following general formula [V], wherein (see diagramm)(see diagramm) R **3 is a substituted hydrocarbon group, a substituted heterocyclic group, an unsubstituted hydrocarbon group, or an unsubstituted heterocyclic group and R **4 is an electron-withdrawing group.
[claim2]
2. A diamino acid derivative starting material, said diamino acid derivative starting material being a compound represented by the following general formula [1], wherein (see diagramm) R **2 is a substituted hydrocarbon group or an unsubstituted hydrocarbon group and all of R **2 may be identical to each other, or may differ from each other and the fluorenyl group is a ring-substituted fluorenyl group or a ring-unsubstituted fluorenyl group.
[claim3]
3. A diamino acid derivative starting material, said diamino acid derivative starting material being a compound represented by the following general formula [II], wherein (see diagramm)(see diagramm) R **2 is a substituted hydrocarbon group or an unsubstituted hydrocarbon group and all of R **2 may be identical to each other, or may differ from each other; R **3 is a substituted hydrocarbon group, a substituted heterocyclic group, an unsubstituted hydrocarbon group, or an unsubstituted heterocyclic group; R **4 is an electron-withdrawing group which is an alkoxycarbonyl group, an acyl group, an arylsulfonyl group or an alkylsulfonyl group, and the fluorenyl group is a ring-substituted fluorenyl group or a ring-unsubstituted fluorenyl group.
[claim4]
4. The diamino acid derivative starting material according to claim 2 or 3, wherein said R **2 is a hydrocarbon group having a carbon number of 1 to 8.
[claim5]
5. A manufacturing method of diamino acid derivatives, said manufacturing method comprising removing a fluorenyl group of a diamino acid derivative starting material represented by the following general formula [II], wherein (see diagramm)(see diagramm) R **2 is a substituted hydrocarbon group or an unsubstituted hydrocarbon group and all of R **2 may be identical to each other, or may differ from each other.
R **3 is a substituted hydrocarbon group, a substituted heterocyclic group, an unsubstituted hydrocarbon group, or an unsubstituted heterocyclic group; R **4 is an electron-withdrawing group and the fluorenyl group is a ring-substituted fluorenyl group or a ring-unsubstituted fluorenyl group.
[claim6]
6. The method according to claim 1 or 5, wherein said R **2 is a hydrocarbon group having a carbon number of 1 to 8.
[claim7]
7. A manufacturing method of starting materials of diamino acid derivatives represented by the following general formula [IV], wherein (see diagramm)(see diagramm) R **1 is a substituted hydrocarbon group or an unsubstituted hydrocarbon group; R **3 is a substituted hydrocarbon group, a substituted heterocyclic group, an unsubstituted hydrocarbon group, or an unsubstituted heterocyclic group; R **4 is an electron-withdrawing group and the fluorenyl group is a ring-substituted fluorenyl group or a ring-unsubstituted fluorenyl group
said manufacturing method comprising reacting a compound represented by the following general formula [III], wherein (see diagramm) R **1 is a substituted hydrocarbon group or an unsubstituted hydrocarbon group and the fluorenyl group is a ring-substituted fluorenyl group or a ring-unsubstituted fluorenyl group
with a compound represented by the following general formula [V], wherein (see diagramm) R **3 is a substituted hydrocarbon group, a substituted heterocyclic group, an unsubstituted hydrocarbon group, or an unsubstituted heterocyclic group and R **4 is an electron-withdrawing group.
[claim8]
8. The manufacturing method of the diamino acid derivative starting materials according to claim 1 or 7, wherein the reaction between the compound represented by said general formula [III] and the compound represented by said general formula [V], and the reaction between the compound represented by said general formula [I] and the compound represented by said general formula [V], respectively, is conducted in the presence of an optically active basic catalyst.
[claim9]
9. The manufacturing method of the diamino acid derivative starting materials according to claim 8, wherein said optically active basic catalyst is any member selected from a group of optically active guanidine compounds.
[claim10]
10. The manufacturing method of the diamino acid derivative starting materials according to claim 8, wherein said optically active basic catalyst is any member selected from a group of optically active basic catalysts configured using MX 2 (M is Be. Mg, Ca, Sr, Ba or Ra; X is an arbitrary group) and compounds represented by the following general formula [VI], wherein (see diagramm) R **7, R **8, R **9, and R **10 each represents a substituted cyclic group or an unsubstituted cyclic group, wherein R **9 and R **10 form a ring in some cases, and they do not form a ring in some cases.
[claim11]
11. A diamino acid derivative starting material, said diamino acid derivative starting material being a compound represented by the following general formula [III], wherein (see diagramm) R **1 is a substituted hydrocarbon group or an unsubstituted hydrocarbon group and the fluorenyl group is a ring-substituted fluorenyl group or a ring-unsubstituted fluorenyl group.
[claim12]
12. A diamino acid derivative starting material, said diamino acid derivative starting material being a compound represented by the following general formula [IV], wherein (see diagramm) R **1 is a substituted hydrocarbon group or an unsubstituted hydrocarbon group; R **3 is a substituted hydrocarbon group, a substituted heterocyclic group, an unsubstituted hydrocarbon group, or an unsubstituted heterocyclic group; R **4 is an electron-withdrawing group which is an alkoxycarbonyl group, an acyl group, an arylsulfonyl group or an alkylsulfonyl group, and the fluorenyl group is a ring-substituted fluorenyl group or a ring-unsubstituted fluorenyl group.
[claim13]
13. The diamino acid derivative starting material according to claim 11 or 12, wherein said R **1 is a hydrocarbon group having a carbon number of 1 to 8.
[claim14]
14. The diamino acid derivative starting material according to claim 3 or 12, wherein said R **3 is a hydrocarbon group having a carbon number of 1 to 8 or a heterocyclic group having a carbon number of 1 to 8.
[claim15]
15. A manufacturing method of diamino acid derivatives, said manufacturing method comprising removing a fluorenyl group of a diamino acid derivative starting material represented by the following general formula [IV], wherein (see diagramm) R **1 is a substituted hydrocarbon group or an unsubstituted hydrocarbon group; R **3 is a substituted hydrocarbon group, a substituted heterocyclic group, an unsubstituted hydrocarbon group, or an unsubstituted heterocyclic group; R **4 is an electron-withdrawing group and the fluorenyl group is a ring-substituted fluorenyl group or a ring-unsubstituted fluorenyl group.
[claim16]
16. The method according to claim 5 or 15, wherein said fluorenyl group is removed with an acidic process.
[claim17]
17. The method according to claim 7 or 15, wherein said R **1 is a hydrocarbon group having a carbon number of 1 to 8.
[claim18]
18. The method according to claim 1, 5, 7 or 15, wherein said R **3 is a hydrocarbon group having a carbon number of 1 to 8 or a heterocyclic group having a carbon number of 1 to 8.
[claim19]
19. The method according to claim 1, 5, 7 or 15, wherein said electron-withdrawing group is an alkoxycarbonyl group, an acyl group, an arylsulfonyl group, or an alkylsulfonyl group.
  • Applicant
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
  • Inventor
  • KOBAYASHI SHU
  • YAMASHITA YASUHIRO
  • SEKI KAZUTAKA
IPC(International Patent Classification)
Reference ( R and D project ) ERATO KOBAYASHI Highly Functionalized Reaction Environments AREA
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