Process for the preparation of l-proline derivatives

Details Process for the preparation of l-proline derivatives Process for the preparation of l-proline derivatives

1994-01-13

1995-12-05

Haley, Jacqueline

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D20712

Patent

active

054730813

ABSTRACT:
An L-proline derivative represented by: ##STR1## wherein R.sub.2 represents a lower alkyl group is prepared by reacting L-proline with a D-.alpha.-alkyl-.beta.-acylthiopropionic acid halide, ##STR2## wherein R.sub.1 represents an acyl group, X represents a halogen atom and R.sub.2 has the same meaning as defined above. The halide is added to an aqueous medium containing L-proline and a condensation agent for deacidification. The halide and L-proline are reacted while the reaction temperature and pH are maintained at 12.degree. C. or lower and within a range of 10.5-11.5, whereby a compound represented by: ##STR3## wherein R.sub.1 and R.sub.2 have the same meanings as defined above is obtained. The resulting compound is then subjected to deacylation under strong alkaline conditions without being isolated from the reaction mixture, thereby yielding the target L-proline derivative.

REFERENCES:
Chemical Abstracts, vol. 95, No. 21, 181197z, Nov. 23, 1981, "Proline Derivatives as Antihypertensives".
Chemical Abstracts, vol. 106, No. 3, 19061z, Jan. 19, 1987, I. Linan Castellet, "1-(3-Mercapto-2-D-Methylpropanoyl)-L-Proline".
Chemical Abstracts, vol. 95, No. 7, 62706e, Aug. 17, 1981, "N-(D-(-Methyl-.beta.-Mercaptopropionyl)-L-Proline Derivatives".
Chemical Abstracts, vol. 109, No. 3, 23391m, Jul. 18, 1988, J. M. Torres Esteban, et al., "Process for the Preparation of 3-Mercapto-2(S)-Methylpropionyl-L-Proline (Captopril)".
Chemical Abstracts, vol. 113, No. 17, 153042s, Oct. 22, 1991, J. M. Moniot, "Preparation of N-[2-(Mercaptomethyl)Propionyl ]-L-Proline".
Chemical Abstracts, 116, No. 3, 21464h, Jan. 20, 1992, X. Qi, et al., "Improved Synthesis of Captopril", Jun. 5, 1991.

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