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US 8,053,590 B2Granted
Method for producing enantiomeric form of 2,3-diaminopropionic acid derivatives
AssigneeSanofi-Aventis Deutschland GmbH
InventorsJoerg Rieke-Zapp, Guenter Billen
Life of this patent
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Abstract
The invention relates to a method for producing enantiomers form of 2,3-diaminopropionic acid derivatives of formula (I) by asymmetric hydrogenation from compounds of formula (II).
Claims16
A compound of the formula IV:
- where:
- R1 and R2 are the same or different and are each independently:
- —(C6-C14)-aryl where aryl is unsubstituted or mono-, di- or trisubstituted independently by R11,
- where R11 is
- F, Cl, I or Br,
- —(C1-C4)-alkyl,
- —CN,
- —CF3,
- —OR5 in which R5 is a hydrogen atom or —(C1-C4)-alkyl,
- —N(R5)—R6 in which R5 and R6 are each independently a hydrogen atom or —(C1-C4)-alkyl,
- —C(O)—R5 in which R5 is a hydrogen atom or —(C1-C4)-alkyl, or
- —S(O)x—R5 in which x is the integer zero, 1 or 2, and R5 is a hydrogen atom or —(C1-C4)-alkyl, or
- R1 and/or R2 are a 4- to 15-membered Het ring where the Het ring is unsubstituted or mono-, di- or trisubstituted independently by —(C1-C5)-alkyl, —(C1-C5)-alkoxy, halogen, nitro, amino, trifluoromethyl, hydroxyl, hydroxy-(C1-C4)-alkyl, methylenedioxy, ethylenedioxy, formyl, acetyl, cyano, hydroxycarbonyl, aminocarbonyl or —(C1-C4)-alkoxycarbonyl;
- R3 is:
- —(C6-C14)-aryl in which aryl is unsubstituted or mono-, di- or
- trisubstituted independently by —NO2, —O—(C1-C4)-alkyl, F, Cl or bromine;
- or
- —O—CH(R7)-aryl in which aryl is unsubstituted or mono-, di- or
- trisubstituted independently by —NO2, —O—CH3, F, Cl or bromine,
- in which R7 is a hydrogen atom or —(C1-C4)-alkyl;
- R4 is:
- a hydrogen atom;
- —(C1-C4)-alkyl;
- or
- —CH(R8)-aryl
- in which R8 is a hydrogen atom or —(C1-C4)-alkyl.
23 more elements
Dependencies are inferred from the claim text.