Merck + Co., Inc.

George G Hazen

Ralph P Volante

Earl M Chamberlin

Warren K Russ, Jr

Meyer Sletzinger

Raymond Cvetovich

Kenneth E Wilson

Mallory F Loewe

Jean M Wyvratt

Frederick W Bollinger

A process is described for the synthesis of 3(S)-4(R)-3-[1(S)-hydroxyethyl]-4-(alkoxycarbonylmethyl)-azetidin-2-one (II) which is a useful intermediate in the synthesis of carbapenem antibiotics.

Cyclization process for synthesis of a beta-lactam carbapenem

This invention relates to a novel and improved process for preparing .alpha.-(trichloromethyl) benzyl alcohols, particularly, trichloromethyl-3-nitrobenzyl alcohol a key intermediate useful in the preparation of clorsulon (4-amino-6-(trichloroethenyl)-1,3-benzene-disulfonamide) via a base-catalyzed condensation reaction of benzaldehydes and chloroform.

Novel process for preparing .alpha.-(trichloromethyl)benzyl alcohols

Disclosed is a mild, efficient, stereo-selective process for a one step conversion of primary and secondary alcohols to their corresponding thiol ester and thiol derivatives with inversion of configuration. The process comprises the reaction of the alcohol in question (4), the thiolacid of choice (5) in the presence of adduct 3; the resulting thiol ester 6 may be converted to the free thiol 7 by hydrolysis or reductive methods: ##STR1##

Process for the conversion of primary and secondary alcohols to their

Disclosed is a novel class of substituted and unsubstituted benzyl formimidates, represented in a convenient acid addition salt form (I); and the use of these reagents in the preparation of the antibiotic N-formimidoyl thienamycin (II): ##STR1## wherein A is a non-critical anion such as chloro, bromo, hydrogen sulfate or an alkyl aralkyl or aryl sulfonate, wherein the alkyl moiety has 1-6 carbon atoms and the aryl moiety is phenyl, for example; n is 0, 1 or 2; and X is independently selected from nitro, halo (chloro, bromo, fluoro, and iodo), loweralkyl having from one to six carbon atoms, phenyl, and phenylalkyl having from 7-12 carbon atoms, and --COOR, wherein R is hydrogen or loweralkyl having from one to six carbon atoms.

Process for the preparation of N-formimidoyl thienamycin and reagents

Disclosed are substituted benzenesulfonylazides (I) which are useful as diazo transfer reagents. ##STR1## R.degree.=C.sub.12 H.sub.25

Substituted benzenesulfonylazides

A process for preparing (1-oxo-2-cyclopentyl-2-methyl-6,7-dichloro-5-indanyloxy)acetic acid comprising reacting 5-cyclopentyl-5-methyl-2-cyclopentenone with a 4-carbon conjugated (open or cyclic) diene bearing vicinal chlorines adjacent to an ether group; aromatizing the resulting adduct to yield the desired indanone.

Process for preparing

Process for preparing (1-oxo-2-phenyl, halophenyl or thienyl-2-methyl-6,7-dichloro-5-indanyloxy)acetic acid, pharmaceutically acceptable salt, ester and amide derivatives thereof and intermediate 5-ether derivatives thereof comprising reacting under Friedel-Crafts conditions a 2-phenyl, halophenyl or thienyl-2-propionyl halide or an anhydride thereof with an ether derivative of 2,3-dichlorophenyl; and reacting the resulting propiophenone with formaldehyde in the presence of acid to yield the desired indanone.

Process for preparing (1-oxo-2-phenyl, halophenyl or

Process for preparing [1-oxo-2-cyclopentyl(or 2-isopropyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid, pharmaceutically acceptable salt, ester and amide derivatives thereof and intermediate 5-ether derivatives thereof comprising reacting under Friedel-Crafts conditions a 2-cyclopropyl-or 2-isopropylpropionyl halide or an anhydride thereof with an ether derivative of 2,3-dichlorophenol; and reacting the resulting propiophenone with formaldehyde in the presence of acid to yield the desired indanone.

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Westfield, NJ, United States of America

George G Hazen