Process for the industrial synthesis of (2S, 3aS, 7aS) 2-carboxy

Details Process for the industrial synthesis of (2S, 3aS, 7aS) 2-carboxy Process for the industrial synthesis of (2S, 3aS, 7aS) 2-carboxy

1988-09-16

1990-06-19

Brown, Johnnie R.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548491, C07D20934

Patent

active

049355252

ABSTRACT:
Process for the industrial synthesis of (2S, 3 7aS)-2-carboxyperhydroindole by reduction of 2-carbox indole or of one of its esters to (R,S)-2-carboxyindo or of one of its esters which, after saponification, converted into the acid, the S isomer cf (R,S)-2-carboxyindoline being obtained by precipitation from the mixture of the two (R) and (S) isomers, in the presence of (+) methylbenzylamine, (S)-2-carboxyindoline being in its turn subjected to catalytic hydrogenation to give (2S, 3aS,7aS)-2-carboxyperhydroindole, after separation of (2S,3aR,7aR) isomer by crystallization.
Application to the synthesis of carboxyalkyl d peptides capable of being employed in therapeutics.

REFERENCES:
patent: 4303583 (1981-12-01), Kim
patent: 4520205 (1985-05-01), Buzby
patent: 4659838 (1987-04-01), Lerch

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