Process for the preparation of haloalkyllactones

Details Process for the preparation of haloalkyllactones Process for the preparation of haloalkyllactones

1990-06-04

1993-10-19

Ivy, C. Warren

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549321, 549323, 549324, 549326, C07D30733

Patent

active

052546977

ABSTRACT:
The invention provides a novel process for the manufacture of enantiomerically-pure halolactones of the formula I which are useful for the production of certain 5-amino-4-hydroxyvaleric acid derivatives, themselves valuable intermediates in the production of compounds which are renin inhibitors. The process involves a diastereoselective alkylation of an oxazolidinone of the formula III, followed by a highly stereoselective and novel halolactonisation of an oxazolidinone of the formula II. Certain of the oxazolidinones of the formula II are novel and are provided as a further feature of the invention. The invention also provides a novel process for the production of the pharmaceutically-useful 5-amino-4-hydroxyvaleric acid derivatives of formula VI.

REFERENCES:
patent: 4880781 (1989-11-01), Hester, Jr. et al.
Evans, D. A., Aldrichimica Acta, vol. 15, No. 2, 1982, pp. 23-31.
Herold et al. II, J. Org. Chem. vol. 54, No. 5, Mar. 3, 1989 pp. 1178-1185.
Baker et al., Journal fo the Chemical Society, Perkin Transactions I, No. 1, Jan. 1988; pp. 85-97, Royal Society of Chemistry, "Enantiospecific synthesis of the spiroacetal moieties of avermectins A1b, B1b, A1a, B1a, A2b, B2b, A2a, and B2a and milbemcins alpha7 and alpha8", p. 96, compound 44.

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