Process for preparing optically active 3-azidocarboxylic acid derivatives and 3-aminocarboxylic acid derivatives

Abstract

A process for enantioselectively preparing 3-azidocarboxylic acid derivatives comprises reacting 3-sulfonatocarboxylic acid derivatives with an alkali metal azide in a solvent selected from the group comprising certain carboxamides; a solvent mixture which comprises such carboxamides; a solvent mixture of water and a solvent miscible homogeneously with water; water with the proviso that the addition of a phase transfer catalyst is not used in the reaction in water; and DMSO. The resulting products are optionally reduced to 3-aminocarboxylic acid derivatives.

Description

Claims

1. A process for enantioselectively preparing 3-azidocarboxylic acid derivatives of the general formula (III)

2. The process of claim 1, wherein R is an alkyl radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl and butyl.

3. The process of claim 1, wherein X is hydrogen (H).

4. The process of claim 1, wherein the reaction is performed with 1-2 equivalents of sodium azide based on the sulfonate of the general formula (II) used.

5. The process of claim 1, wherein the reaction is performed in a solvent mixture composed of water and a solvent which is miscible homogeneously with water and is selected from the group comprising dimethyl sulfoxide, dimethylformamide, formamide or N-methylformamide.

6. The process of claim 1, wherein the reaction is performed in formamide or N-methylformamide.

7. The process of claim 1, wherein the reaction is performed in DMSO.

8. The process of claim 1, wherein a resulting 3-azidocarboxylic acid derivatives are reduced in a subsequent step to 3-aminocarboxylic acid derivatives of the general formula (IV)

9. The process of claim 8, wherein the 3-azidocarboxylic acid derivatives or 3-aminocarboxylic acid derivatives are obtained in enantiomerically pure or enantiomerically enriched form.

10. The process of claim 9, wherein R1 is a linear or branched, saturated or unsaturated alkyl or aralkyl radical which is cyclic or contains cyclic groups and wherein R1 optionally substituted by Q.

11. The process of claim 9, wherein R1 is selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl and benzyl.

12. A process for enantioselectively preparing 3-azidocarboxylic acid derivatives of the general formula (III)

13. The process of claim 12, wherein X is hydrogen (H).

14. The process of claim 12, wherein the reaction is performed with 1-2 equivalents of sodium azide based on the sulfonate of the general formula (II) used.

15. The process of claim 12, wherein the reaction is performed in formamide or N-methylformamide.

16. The process of claim 12, wherein a resulting 3-azidocarboxylic acid derivatives is reduced in a subsequent step to 3-aminocarboxylic acid derivatives of the general formula (IV)

17. The process of claim 16, wherein the 3-azidocarboxylic acid derivatives or 3-aminocarboxylic acid derivatives are obtained in enantiomerically pure or enantiomerically enriched form.

18. The process of claim 16, wherein R1 is a linear or branched, saturated or unsaturated alkyl or aralkyl radical which is cyclic or contains cyclic groups and wherein R1 optionally substituted by Q.

19. The process of claim 16, wherein R1 is selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl and benzyl.

20. A process for enantioselectively preparing 3-azidocarboxylic acid derivatives of the general formula (III)