Processes for the preparation of 5-amino-4-hydroxy-valeric acid

Details Processes for the preparation of 5-amino-4-hydroxy-valeric acid Processes for the preparation of 5-amino-4-hydroxy-valeric acid

1989-10-24

1991-04-23

Raymond, Richard L.

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

Organic compounds

Four or more ring nitrogens in the bicyclo ring system

546248, 548342, 548502, 548562, 556437, 558441, 558444, 560 37, 560 55, 560104, 560128, 560147, 560149, 560150, 560152, 560168, 560172, 560174, 560183, C07C 5703, C07C26530

Patent

active

050101897

ABSTRACT:
The invention relates to novel processes and intermediates for the preparation of 5-amino-4-hydroxyvaleric acid derivatives of the formula ##STR1## in which R.sup.1 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl or the radical of a natural amino acid, R.sup.2 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl, amino, hydroxy, mercapto, sulphinyl, sulphonyl or the radical of a natural amino acid, and R.sup.3 represents optionally substituted hydroxy or amino, by sigmatropic rearrangement of a suitable allyl ester, halolactonization of the resulting .gamma.,.delta.-unsaturated acid or of a suitable derivative thereof, exchange of halogen for a nitrogen-containing nucleophile, opening of the lactone ring and freeing of the amino group. Compounds of the formula I are starting materials for the preparation of renin-inhibitors which have an anti-hypertensive action.

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