Processes for the preparation of 5-amino-4-hydroxyvaleric acid d

Details Processes for the preparation of 5-amino-4-hydroxyvaleric acid d Processes for the preparation of 5-amino-4-hydroxyvaleric acid d

1987-08-13

1990-02-06

Shippen, Michael L.

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

Organic compounds

Amino nitrogen containing

544130, 544132, 544139, 544159, 544162, 544163, 544168, 544171, 544175, 544176, 546 14, 546208, 546210, 546226, 546233, 546230, 546235, 548342, 548495, 548540, 548568, 548573, 549321, 549323, 549324, 556416, 556418, 556419, 558254, 558255, 558404, 558406, 558436, 558437, 558438, 558441, 558445, 560 12, 560 16, 560 29, 560 34, 560 35, 560 39, 560118, 560120, 560121, 560125, 560126, 560147, 560148, 560150, 560153, 560168, 560169, 560170, 560312, 562426, 562430, 562439, 562440, 562444, 562448, 562503, 562507,

Patent

active

048989770

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, halolactonisation 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.

REFERENCES:
patent: 4031115 (1977-06-01), Kurkov
patent: 4487963 (1984-12-01), Bock
Dowle et al., Chem. Society Reviews, vol. 8, p. 171 (1979).
Herold et al., J. Org. Chem. vol. 54, p. 1178 (1989).

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