Process for preparing (trans)-4-substituted-dl-proline derivativ

Details Process for preparing (trans)-4-substituted-dl-proline derivativ Process for preparing (trans)-4-substituted-dl-proline derivativ

1989-01-17

1990-06-26

Brust, Joseph Paul

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548533, 548535, C07D20708, C07D20746

Patent

active

049373552

ABSTRACT:
A process is provided for preparing (trans)-4-phenyl-DL-proline derivatives, which are useful in preparing certain angiotensin converting enzyme inhibitors, which process involves reacting an ester of the structure ##STR1## wherein X is a leaving group such as tosylate, R.sup.3 is lower alkyl, R is cyclohexyl, phenyl or substituted phenyl, and R.sup.1a is a protecting group, with a potassium amide base such as potassium hexamethyldisilazide under reduced temperatures to form the trans-4-substituted proline ester derivative of the structure ##STR2## then hydrolyzing the proline ester to the acid of the structure ##STR3## and removing the R.sup.1a nitrogen protecting group to form the unprotected acid of the structure ##STR4##

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Ihara et al., J. Chem. Soc. Perkin Trans I (1986), pp. 1543-1549.
Shiozaki et al., Heterocycles, vol. 22, No. 8 (1984), pp. 1725-1726.
J. Med. Chem (88) 31/6, 1148-60.
Helvetica Chimica Acta, vol. 64, Fasc. 7 (1981), Nr. 215, pp. 2203-2218.
Tetrahedron Letter, vol. 27, No. 47, pp. 5707-5710 (1986).

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