Merck + Co., Inc.

Thomas M Liu

Meyer Sletzinger

Ichiro Shinkai

David G Melillo

Kenneth M Ryan

Ralph P Volante

Thomas R Verhoeven

Edward G Corley

James M McNamara

Robert A Reamer

Joseph E Lynch

Leonard M Weinstock

Joseph S Amato

Robert S Hoerrner

Joel J Friedman

This invention relates to the synthesis of a bicyclic ketoester compound of the formula 1 obtained by cyclizing a diazo compound of formula 2: in the presence of a rhodium catalyst. ##STR1## By adding an effective amount of a Lewis acid to the cyclization reaction, the reaction selectively produces the 1-beta methyl isomer, and epimerization of the 1-beta methyl compound to the 1-alpha isomer is minimized.

Process for synthesizing carbapenem intermediates using a rhodium

Anti-ulcer agents having a methylsulfinyl bridge between a substituted pyridine moiety and a substituted benzimidazole moiety are prepared by oxidizing the corresponding compounds, having a methylthio bridge, with magnesium monoperoxyphthalate in a suitable solvent. The reaction may be run in an aromatic hydrocarbon solvent, wherein the product may crystallize out of the reaction solution and may be directly isolated by filtration.

Process for the preparation of antiulcer agents

This invention relates to a novel process for the preparation of 3-hydroxy-3-methylglutarylcoenzyme A (HMG-CoA) reductase inhibitors which contain a 4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one moiety, such as compactin and mevinolin, by utilizing an alkyl 4-cyano-3(R)-hydroxybutanoate as a chiral synthon for the stereospecific introduction of the 4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one moiety.

Process for the preparation of HMG-CoA reductase inhibitors and

This invention relates to a novel process for the preparation of 3-hydroxy-3-methylglutarylcoenzyme A (HMG-CoA) reductase inhibitors which contain a 4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one moiety, such as compactin and mevinolin, by utilizing an alkyl 4-halo-3(S)-hydroxybutanoate as a chiral synthon for the stereospecific introduction of the 4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one moiety.

Process for the preparation of HMG-CoA reductase inhibitors

Disclosed is a process for the stereocontrolled total synthesis of thienamycin via intermediates II and IIa: wherein R is a readily removable carboxyl protecting group.

Synthesis of thienamycin via (3SR, 4RS)-3-[1

Disclosed is a process for the stereocontrolled total synthesis of thienamycin via intermediates II and IIa: ##STR1## wherein R is a readily removable carboxyl protecting group.

1-Hydroxyethyl-2-amino pentanedioic acid derivatives

Disclosed is a process for the stereocontrolled total synthesis of thienamycin from acetone dicarboxylate via intermediate II: ##STR1## wherein R is a readily removable carboxyl protecting group.

Hydroxy amino dicarboxylic acids and esters

Disclosed is a process for the stereocontrolled total synthesis of thienamycin, which synthesis proceeds via intermediate II: ##STR1## wherein R.sup.3 is a readily removable carboxyl protecting group.

Synthesis of thienamycin via esters of (3SR,

Intermediate for synthesis of thienamycin via (3SR, 4RS)-3-[1

Intermediate for the preparation of thienamycin

Disclosed is 2 and a process for its preparation: ##STR1## It is useful in the synthesis of N-formimidoyl thienamycin; R.sup.2 is hydrogen or a protecting group.

Process for the preparation of N-protected N-formimidoyl

Disclosed is a process for preparing N-protected 2-aminoethanethiol which proceeds via the silyl covered sulfur intermediate: ##STR1## wherein R.sup.1 is triorganosilyl and R.sup.2 is a readily removable N-protecting group.

Process for preparing N-protected 2-aminoethanethiol

Disclosed is a process for the stereocontrolled total synthesis of thienamycin, which synthesis proceeds via intermediate II: ##STR1## wherein R is a readily removable carboxyl protecting group; and ##STR2## is a readily removable acyl group.

Growing community of inventors

Westfield, NJ, United States of America

Thomas M Liu