Process for preparation of dipeptides
OwnerJohn C. Hubbsinventor
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Abstract
Disclosed is a process for synthesis of a dipeptide such as N-acetyl-L-.alpha.-aspartyl-L-phenylalanine methyl ester wherein one amino acid serves as a chiral template which allows for synthesis of a second amino acid residue to form said dipeptide. The process involves several novel steps such as a nucleophile addition step. In addition, several novel intermediates are described.
Claims8
A process comprising contacting a compound of the formula ##STR24## with a nucleophile, in the presence of an appropriate base, under conditions such that a compound is formed of the formula:
- ##STR25## wherein R and R.sup.1 are different and are each, independently, hydrogen, alkyl, hydroxy, aryl, C.sub.1 to C.sub.10 substituted alkyl, C.sub.1 to C.sub.10 alkoxy, C.sub.7 to C.sub.12 substituted arylalkyl, C.sub.1 to C.sub.10 acyl, C.sub.1 to C.sub.10 carboxyalkyl or C.sub.1 to C.sub.10 acyloxy;
- Z is a nitrogen-protecting group;
- Z.sup.1 is hydrogen or a nitrogen-protecting group provided that the ability of the Z substituent to withdraw electrons is greater than that of the Z.sup.1 substituent;
- and Q is a residue of a nucleophile.
A process comprising contacting a compound of the formula ##STR26## with a nucleophile, in the presence of an appropriate base, under conditions such that a compound is formed of the formula:
- ##STR27## wherein R is C.sub.1 to C.sub.10 acyloxy, R.sup.1 is aryl, Z is acyl or acyloxy, and R.sup.4 is hydrogen, alkyl, or aryl.
Dependencies are inferred from the claim text.