Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1990-01-19
1991-04-16
Berch, Mark L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
558107, C07B 5300, C07F 9572, C07F 932
Patent
active
050083996
ABSTRACT:
An increase in the disastereoselectivity resulting from the reaction of a phosphinic acid ester of the formula ##STR1## with the halo ester of the formula ##STR2## is achieved by carrying out the reaction in the presence of 4-methylmorpholine, diazabicyclooctane, quinuclidine, 1-methylpyrolidine, or cinchonidine. After removal of the R.sub.3 protecting group and fractional crystallization, the resulting desired diastereomeric pair can be resolved, and the desired isomer can be coupled to 4-substituted L-proline to give compounds possessing angiotensin converting enzyme inhibition activity. In particular, the process is useful in producing the antihypertensive agent fosinopril sodium in increased yields.
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Crilley, Tet. Letters 30, 885-8 (1989).
Jaeger, Chem. Abs. 90, 134487 (1979).
Ohtauka et al., "New Condensing Reagents For Stereospecific Synthesis of Dinucleoside Monophosphate Aryl Esters", Tetrahedron Letters, vol. 22, No. 45, p. 4483-4486 (1981).
Berch Mark L.
Davis Stephen B.
E. R. Squibb & Sons Inc.
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