Production of intermediates for enzyme inhibitors

Details Production of intermediates for enzyme inhibitors Production of intermediates for enzyme inhibitors

1980-06-16

1982-04-20

Ford, John M.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

560105, 560174, C07C11708, C07C 6974, C07C 6966

Patent

active

043258778

ABSTRACT:
5-Amino-4-oxo-pentanoic acids of the formula ##STR1## wherein R is CF.sub.3, CHF.sub.2 or CH.sub.2 F; R.sub.1 is H or akyl of 1-4 carbon atoms; and R.sub.2 is H or alkyl or 1-4 carbon atoms or benzyl, which are intermediates to ACE inhibitors or elastase inhibitors, are produced by reacting a 1-(methylthio)-1-methylsulfinyl)-2-R.sub.1 -ethylmetal with an ester of a 3-R-acrylic acid; optionally R.sub.2 -alkylating the thus-produced ester enolate anion of 4-(methylsulfinyl)-4-(methylthio)-5-R.sub.1 R-pentanoic acid followed by splitting off of methylsulfinic acid; reacting the thus-produced 2-R.sub.2 -5-R.sub.1 -4-(methylthio)-3-R-4-pentenoic acid ester with a source of Br.sup.+ to produce a 5-bromo-substituted acid or ester thereof otherwise corresponding to the desired 5-amino-4-oxo-pentanoic acid; and replacing the bromine atom with an amino group, e.g., via the corresponding 5-azido- and 5-N-acylamino- compounds, with hydrolysis of the ester group, if still remaining.

REFERENCES:
Price et al., J. Org. Chem., vol. 30, pp. 2064 to 2067 (1965).
Rappe, Chem. Abstracts, vol. 54, cols. 17259 to 17260 (1960).
Barton et al., Chem. Abstracts vol. 57, cols. 909-910 (at col. 910 between h and i) 1962.
Chemical Abstracts, Eighth Collective Index, subjects Tripet-Z, p. 32647S.

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