Method for making phosphinic acid intermediates

Details Method for making phosphinic acid intermediates Method for making phosphinic acid intermediates

1985-01-22

1986-07-22

Sutto, Anton H.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

558136, 558307, 548113, 560105, 2605024R, 2605025D, C07F 932

Patent

active

046020926

ABSTRACT:
A method is provided for preparing phosphinic acid prodrug intermediates which are useful in preparing phosphinic acid angiotensin-converting enzyme inhibitors which method includes the step of coupling a phosphonous acid or its ester of the structure ##STR1## wherein R is H or lower alkyl and R.sup.1 is lower alkyl, aryl, arylalkyl, cycloalkyl or cycloalkylalkyl, with an alkylating agent of the structure ##STR2## wherein Hal is Cl, Br or I, n is 0 or 1, R.sup.2 is H or lower alkyl, and Z is H, lower alkyl, --CO.sub.2 R.sup.3 (wherein R.sup.3 is H or lower alkyl), ##STR3## (wherein R.sup.4 is H, lower alkyl, aryl or arylalkyl), --CN, or ##STR4## (wherein R.sup.5 and R.sup.6 may be the same or different and are selected from the group consisting of H, lower alkyl, aryl, aryl-lower alkyl, cycloalkyl or cycloalkylalkyl and at least one of R.sup.5 and R.sup.6 is other than H, or R.sup.5 and R.sup.6 can be taken with the N-atom to form a 5-, 6- or 7-membered heterocyclic ring which 5-, 6- or 7-membered N-containing ring may or may not contain a CO.sub.2 R.sup.3 group and which 5- or 6-membered N-containing ring may or may not be fused to an aryl ring), in the presence of a silylating agent, to form the phosphinic acid intermediate of the structure ##STR5## wherein R, R.sup.1, R.sup.2, n and Z are as defined above.

REFERENCES:
patent: 4168267 (1979-09-01), Petrillo, Jr.
patent: 4316905 (1982-02-01), Krapcho
patent: 4316906 (1982-02-01), Ondetti et al.
patent: 4337201 (1982-06-01), Petrillo
Thottathil et al., "Tetrahedron Letters", vol. 25, No. 42, pp. 4737-4740, (1984).

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