Xiaoyong Fu - Edison NJ, US Jianguo Yin - Edison NJ, US Timothy McAllister - Westfield NJ, US Cesar Colon - Rio Piedras PR, US
International Classification:
C07C069/73
US Classification:
560/060000, 560/183000
Abstract:
A single batch process for preparing (R)-benzyl-4-hydroxy-2-pentynoate by reacting (R)-3-butyn-2-ol with 1,1,1,3,3,3-hexamethyldisilazane to silylate the starting alcohol, followed by deprotonation with an alkyl lithium compound, then a reaction with a haloformate compound, and finally a hydrolysis reaction to arrive at the product ester.
Process For Preparing Albuterol, Acetal, Hemi-Acetal, And Hydrates Of Arylglyoxal Intermediates Thereof
T. K. Thiruvengadam - Edison NJ John Chiu - Parsippany NJ Michael Green - Paterson NJ Timothy L. McAllister - Fords NJ Cesar Colon - Rahway NJ Junning Lee - Springfield NJ
Assignee:
Schering Corp. - Kenilworth NJ
International Classification:
C07C 6976 C07F 502
US Classification:
560 53
Abstract:
The preparation of arylethanolamines, and in particular albuterol (salbutamol), together with their novel boron, acetal and hemi-acetal intermediates is described.
Xiaoyong Fu - Edison NJ Timothy L. McAllister - Westfield NJ John S. Chiu - Parsippany NJ Cesar Colon - Rahway NJ
Assignee:
Schering Corporation - Kenilworth NJ
International Classification:
C07D205/08;263/26
US Classification:
540200
Abstract:
This invention provides a process for preparing the hypocholesterolemic compound ##STR1## comprising: (a) reacting p-fluorobenzoylbutyric acid with pivaloyl chloride and acylating the product with a chiral auxiliary to obtain a ketone of formula IV: ##STR2## (b) reducing the ketone of formula IV in the presence of a chiral catalyst to an alcohol: (c) reacting the chiral alcohol of step (b), an imine and a silyl protecting agent, then condensing the protected compounds to obtain a. beta. -(substituted-amino)amide of formula VII: ##STR3## (d) cyclizing the. beta. -(substituted-amino)amide of formula VII with a silylating agent and a fluoride ion catalyst to obtain a protected lactam of the formula VIII: ##STR4## and removing the protecting groups. The intermediates of formulas VII and VIII are also claimed.
Process For The Stereospecific Synthesis Of Azetidinones
Junning Lee - Springfield NJ Timothy McAllister - Fords NJ Cesar Colon - Rahway NJ Derek H. R. Barton - College Station TX Ronald Breslow - Englewood NJ Anantha Sudhakar - East Brunswick NJ
Assignee:
Schering Corporation - Kenilworth NJ
International Classification:
C07D20508
US Classification:
540200
Abstract:
This invention provides an improved process for producing azetidinones. More particularly, this invention provides the steps of producing an trans-azetidinone represented by the formula ##STR1## from a carboxylic acid R. sup. 2 --D--CH. sub. 2 COOH, an aldehyde R. sup. 1 --A--CHO and an amine RNH. sub. 2, by the steps of: (a1) converting a carboxylic acid to the corresponding acid chloride; (b1) deprotonating a chiral oxazolidinone and treating the resulting anion with the product of step (a1); (c1) enolizing the product of step (b1) and condensing with the aldehyde; (d1) hydrolyzing the product of step (c1); (e1) condensing the product of step (d1) with the amine; and (f1) cyclizing the product of step (e1). Alternatively, the process comprises (a2) enolizing the product of step (b1) and condensing, in the presence of a Lewis acid, with a Schiff's base prepared from the aldehyde and the amine; and (b2) cyclizing the product of step (a2).
John S. Chiu - Parsippany NJ Cesar Colon - Roselle Park NJ
Assignee:
Schering Corporation - Kenilworth NJ
International Classification:
A61K 3171 C07H 1522 C07D 704
US Classification:
536 139
Abstract:
A high yielding process for converting 3,2',6'-tri-N-acetyl sisomicin to netilmicin comprising the step of silylating the starting material at the 5,2' positions, and optionally at the 4' position, converting the 1-amino substituent to a 1-N-imino substituent, converting the imino to an ethylamino, deprotecting the compound and recovering netilmicin. Also disclosed are novel intermediate compounds.
Process For Preparing Delta 9, 11 And 21-Chlorocorticosteroids
Xiaoyong Fu - Edison NJ Junning Lee - Gillette NJ Cesar Colon - Rahway NJ
Assignee:
Schering Corporation - Kenilworth NJ
International Classification:
C07J 7500
US Classification:
552581
Abstract:
Described is a process for the regioselective dehydration of 11-hydroxy steroids using PCl. sub. 5, PCl. sub. 3, POCl. sub. 3 or either SO. sub. 2 Cl. sub. 2 and imidazole, or PPh. sub. 3 and CCl. sub. 4. The disclosed process selectively forms. DELTA. sup. 9,11 steroids from either 11-. alpha. - or 11-. beta. -hydroxy steroids, and can also be used for the one-step conversion of 11,21 -dihydroxy steroids to 21-chloro-. DELTA. sup. 9,11 steroids. Also disclosed are processes for the regioselective conversion of 11-. beta. -chloro steroids to. DELTA. sup. 9,11 steroids, and for regioselectively converting an 11,17,21-trihydroxy streoid to a 21-chloro-11,17-dihydroxy steroid.
Process For Preparing Delta 9,11 And 21-Chloro Corticosteroids
Xiaoyong Fu - Edison NJ Junning Lee - Gillette NJ Cesar Colon - Rahway NJ
Assignee:
Schering Corporation - Kenilworth NJ
International Classification:
C07J 500 C07J 700 C07J 7500
US Classification:
552595
Abstract:
Described is a process for the regioselective dehydration of 11-hydroxy steroids using PCl. sub. 5, PCl. sub. 3, POCl. sub. 3 or either SO. sub. Cl. sub. 2 and imidazole, or PPh. sub. 3 and CCl. sub. 4. The disclosed process selectively forms. increment. sup. 9,11 steroids from either 11-. alpha. - or 11-. beta. -hydroxy steroids, and can also be used for the one-step conversion of 11,21-dihydroxy steroids to 21-chloro-. increment. sup. 9,11 steroids.
Cesar Colon (1985-1986), John Bush (1996-2000), Mary Sieli (1975-1979), Patrick Bifulco (1974-1978), Tara Covell (1988-1992), Matthew Troiano (1972-1976)