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Generated: May 20, 2018

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Details for Patent: 3,892,744

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Title: Process for preparing 4-[3-(substituted amino)-2-hydroxypropoxy]-1,2,5-thiadiazoles
Abstract:Preparation of S-3-X-4-(3-substituted amino-2-hydroxypropoxyl)-1,2,5-thiadiazole .beta.-adrenergic blocking agents using as starting material an optically active oxazolidine in the sinister configuration which is reacted with a 3-X-4-RO-1,2,5-thiadiazole.
Inventor(s): Weinstock; Leonard M. (Belle Mead, NJ), Tull; Roger J. (Metuchen, NJ), Mulvey; Dennis M. (Milford, NJ)
Assignee: Merck & Co., Inc. (Rahway, NJ)
Filing Date:Dec 18, 1973
Application Number:05/425,912
Claims:1. A process for the preparation of an optically active thiadiazole in the sinister configuration having the structure S-III, ##SPC8##

comprising the reaction of a compound of structure I with a compound of structure S-II, ##SPC9##

followed by acid hydrolysis wherein the variable radical X is selected from chloro, C.sub.1-3 alkyl, C.sub.1-3 alkoxy, phenyl, benzyl, morpholino, piperidino, hydroxypiperidino, and N-C.sub.1-3 alkyl-1-piperazinyl, Y is a straight or branched chain C.sub.1-5 alkyl; Z is hydrogen or an aliphatic, alicyclic, aromatic or heterocyclic residue of the aldehyde ZCHO used to form the oxazolidine nucleus; and R.sup.3 is alkylsulfonyl, arylsulfonyl or aralkylsulfonyl.

2. A process as in claim 1 wherein the reaction is carried out at a temperature between about 0.degree. to reflux.

3. A process as in claim 2 wherein reactant I is the sodium salt of 3-morpholino-4-hydroxy-1,2,5-thiadiazole and reactant S-II is S-3-tert-butyl-5-(p-toluenesulfonyloxymethyl)-oxazolidine to provide S-(-)-3-morpholino-4-(3-tert-butylamino-2-hydroxypropoxy)-1,2,5-thiadiazol e.

4. A process as in claim 2 wherein reactant I is the sodium salt of 3-morpholino-4-hydroxy-1,2,5-thiadiazole and reactant S-II is S-3-tert-butyl-5-(p-nitrophenylsulfonyloxymethyl)-oxazolidine to provide S-(-)-3-morpholino-4-(3-tert-butylamino-2-hydroxypropoxy)-1,2,5-thiadiazol e.

5. A process as in claim 2 wherein reactant I is the sodium salt of 3-morpholino-4-hydroxy-1,2,5-thiadiazole and reactant S-II is S-3-tert-butyl-5-(p-bromobenzenesulfonyloxymethyl)-oxazolidine to provide S-(-)-3-morpholino-4-(3-tert-butylamino-2-hydroxypropoxy)-1,2,5-thiadiazol e.

6. The process as in claim 2 wherein reactant I is the sodium salt of 3-morpholino-4-hydroxy-1,2,5-thiadiazole and reactant S-II is S-3-tert-butyl-5-(benzenesulfonyloxymethyl) oxazolidine to provide S-(-)-3-morpholino-4-(3-tert-butylamino-2-hydroxypropoxy)-1,2,5-thiadiazol e.

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