Merck + Co., Inc.

Sandor Karady

Meyer Sletzinger

Burton G Christensen

Lovji D Cama

Leonard M Weinstock

Joseph S Amato

Newton L Abramson

Kevin M Anderson

Anthony O King

Richard F Shuman

Alan W Douglas

Edward G Corley

Seemon H Pines

Dean R Bender

Benjamin Marcune

Theresa Rothauser

Robin S Conn

Theresa Y Cheng

An efficient and facile process for the preparation of cyclopropylacetylene from thioanisole and cyclopropyl substituted ketones or aldehydes is disclosed.

Efficient synthesis of cyclopropylacetylene

A novel single-pot trialkylsilyl trifluoromethanesulfonate (R.sub.3 Si-OTf) mediated process produces derivatives of 4-aza 3-keto steroids at the .alpha.-methylenic carbon through electrophilic substitution. These derivatives are useful in the preparation, through elimination of the substituent on the .alpha.-methylene carbon, of .DELTA.-1 olefin 4-aza 3-keto steroids which are potent inhibitors of 5-.alpha. reductase.

Trialkylsilyl trifluoromethanesulfonate mediated .alpha.-methylenic

A novel, facile, and specific process for .alpha.-iodinating or .alpha.-brominating the .alpha.-methylenic carbon of a straight chain, branched chain, or cyclic secondary amide, such as a lactam or an azasteroid, comprises reacting the amide with trialkylsilyl-X (R.sub.3 Si--X), where X is Br, I, or Cl, and R is methyl, ethyl, or n-propyl, in the presence of I.sub.2 or Br.sub.2. The .alpha.-iodo- or .alpha.-bromo-amide is useful for making the .alpha.,.beta.-unsaturated amide through dehydrohalogenation.

Process for iodinating or brominating the .alpha.-methylenic carbon of a

A novel single-pot trialkylsilyl trifluoromethanesulfonate (R.sub.3 Si--OTf) mediated process produces derivatives of 4-aza 3-keto steroids at the .alpha.-methylenic carbon through electrophilic substitution. These derivatives are useful in the preparation, through elimination of the substituent on the .alpha.-methylene carbon, of .DELTA.-1 olefin 4-aza 3-keto steroids which are potent inhibitors of 5-.alpha. reductase.

10,11 Dihydro-11-exo-hydroxy-5-methyldibenzo[a,d]cyclohepten-5,10-imine is prepared in a four step synthesis which uses an electrochemical cyclization to form the 5,10-imine bridge in about a 50% yield.

Process for preparing

This invention relates to a process for preparing .beta.-lactams by electrochemically deblocking N-substituting .beta.-lactams using anodic oxidation.

Process for deblocking N-substituted .beta.-lactams

A process for direct preparation of an enantiomer of a substituted fluorenyloxyacetic acid is disclosed. The acetic acid derivative is useful for treating brain edema.

Preparation of an enantiomer of a substituted fluorenyloxyacetic acid

A novel synthon useful in the conversion of penicillin is a compound of the formula ##STR1## wherein R.sub.3 is a number of the group consisting of trimethyl-silyl, t-butyl dimethyl silyl, trimethyl silyl, methyl, benzyl or nitrobenzyl, and R.sub.5 is the same or different member of the group R.sub.3 is prepared by the naphthalene sulfonyl azide exchange reaction with benzyl acetoacetate, p-nitrobenzylacetoacetate, or methylacetoacetate to obtain the corresponding 2-diazo compound which is then silylated in hexamethyl-disalazine.

Silyl, benzyl, p-nitrobenyl, or methyl esters of diazoacetate, a synthon

A process for preparing .alpha.-alkyl amino acids by enantioretentive .alpha.-alkylation of .alpha.-amino acids is described. The products are bioactive compounds including some useful as therapeutic agents.

Process for preparation of alpha-alkyl amino acids

(+)-5-Methyl-10,11-dihydro-5H-dibenzo[a,d]-cyclohepten-5,10-imine, and its pharmaceutically acceptable salts is useful as an anxiolytic, antidepressant, anticonvulsant, muscle relaxant and in the treatment of mixed anxiety-depression, minimal brain dysfunction and extrapyramidal disorders such as Parkinson's disease. The racemate of the compound is produced by a four-step synthetic process in about 65% yield from 5H-dibenzo[a,d]cyclohepten-5-one.

Process for 5-methyl-10,11-dihydro-5H-dibenzo[a,d]-cyclohepten-5,10-imine

A stereospecific conversion of penicillin to thienamycin, using diisopropylamine borane and magnesium trifluoroacetate to prepare the hydroxyethyl side chain and acetoacetate dianion equivalent disilylethyl to prepare the .beta.-ketoester side chain.

Stereospecific synthesis of thienamycin from penicillin

Substituted-1,2,5-thiadiazole-1-oxides, their preparation and pharmaceutical use as elastase inhibitors are disclosed.

Substituted-1,2,5-thiadiazole-1-oxide compounds, compositions and use

Process and intermediate products useful in the preparation of cephalosporin compounds having a substituent at the 7-position in place of hydrogen are provided. The new cephalosporin compounds are active against various gram-negative and gram-positive organisms.

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Mountainside, NJ, United States of America

Sandor Karady