N-protected/N-substituted-beta-amino-hydroxy sulfonates
AssigneeG. D. Searle & Co.
InventorJoseph J. Wieczorek
Life of this patent
Estimating the term…
Abstract
N-protected/N-substituted alpha-amino aldehydes, which are useful as pharmaceuticals and pharmaceutical intermediates, can be stored and shipped in a more stable form as N-protected/N-substituted-beta-amino hydroxy sulfonates which can be readily converted back into the aldehyde under mild conditions. The present invention relates to N-protected/N-substituted-beta-amino hydroxy sulfonates and their preparation and use.
Claims21
Compound represented by the formula:
- ##STR43## wherein W represents a cation which is capable of forming a sulfate salt;
- R.sup.1 represents alkyl, alkenyl, alkyl substituted with one or more aryl radicals, cycloalkenylalkyl, alkanoyl, haloalkanoyl, aroyl, alkoxycarbonyl, aralkoxycarbonyl, heteroaralkoxycarbonyl or 9-phenylfluoren-9-yl radicals;
- R.sup.2 represents hydrogen, alkyl, alkenyl, aralkyl, cycloalkyl, cycloalkenylalkyl or aryl radicals;
- or --NR.sup.1 R.sup.2 represents heterocyclo or heteroaryl radicals;
- and
- R.sup.3 represents alkyl, haloalkyl, cyanoalkyl, hydroxyalkyl, alkoxyalkyl, aryloxyalkyl, alkylthioalkyl, arylthioalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, cycloalkyl or cycloalkylalkyl radicals;
- or
- R.sup.2 and R.sup.3 together with nitrogen atom and the carbon atom to which they are bonded form a heterocyclo radical.
Process of preparing a compound formula ##STR44## wherein W represent a cation which is capable of forming a sulfate salt;
- R.sup.1 represents alkyl, alkenyl, alkyl substituted with one or more aryl radicals, cycloalkenylalkyl, alkanoyl, haloalkanoyl, aroyl, alkoxycarbonyl, aralkoxycarbonyl, heteroaralkoxycarbonyl or 9-phenylfluoren-9-yl radicals;
- R.sup.2 represents hydrogen, alkyl, alkenyl, aralkyl, cycloalkyl, cycloalkenylalkyl or aryl radicals;
- or --NR.sup.1 R.sup.2 represents heterocyclo or heteroaryl radicals;
- and
- R.sup.3 represents alkyl, haloalkyl, cyanoalkyl, hydroxyalkyl, alkoxyalkyl, aryloxyalkyl, alkylthioalkyl, arylthioalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, cycloalkyl or cycloalkylalkyl radicals;
- or
- R.sup.2 and R.sup.3 together with nitrogen atom and the carbon atom to which they are bonded form a heterocyclo radical;
- wherein said process comprises treating an aldehyde represented by the formula ##STR45## wherein R.sup.1, R.sup.2 and R.sup.3 are as defined above, in an organic solvent with an aqueous solution of HSO.sub.3 W, wherein W is as defined above.
Process of preparing a compound formula ##STR46## wherein R.sup.1 represents alkyl, alkenyl, alkyl substituted with one or more aryl radicals, cycloalkenylalkyl, alkanoyl, haloalkanoyl, aroyl, alkoxycarbonyl, aralkoxycarbonyl, heteroaralkoxycarbonyl or 9-phenylfluoren-9-yl radicals;
- R.sup.2 represents hydrogen, alkyl, alkenyl, aralkyl, cycloalkyl, cycloalkenylalkyl or aryl radicals;
- or --NR.sup.1 R.sup.2 represents heterocyclo or heteroaryl radicals;
- and
- R.sup.3 represents alkyl, haloalkyl, cyanoalkyl, hydroxyalkyl, alkoxyalkyl, aryloxyalkyl, alkylthioalkyl, arylthioalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, cycloalkyl or cycloalkylalkyl radicals;
- or
- R.sup.2 and R.sup.3 together with nitrogen atom and the carbon atom to which they are bonded form a heterocyclo radical;
- wherein said process comprises treating a compound represented by the formula ##STR47## wherein W represents a cation which is capable of forming a sulfate salt;
- and R.sup.1, R.sup.2 and R.sup.3 are as defined above, with an aqueous base solution.
Dependencies are inferred from the claim text.