Merck + Co., Inc.

Seemon H Pines

Robert F Czaja

Edward J Grabowski

Ulf H Dolling

Roger J Tull

Richard F Shuman

George Gal

David D Saperstein

Meyer Sletzinger

Sandor Karady

Newton L Abramson

Theresa Y Cheng

Matthew A Kozlowski

Alan J Rein

A process is disclosed for obtaining manipulated proportions of the (+) and (-) enantiomers of [(6,7-dichloro-2,3-dihydro-2-methyl-1-oxo-2-phenyl-1H-inden-5-yl)oxy]aceti c acid by asymmetric chiral phase transfer catalysis.

Trifluoromethylbenzyl containing quaternary salts

Process for preparing a manipulated enantiomer mixture by asymmetric

Methylvanillyl ketone is prepared from a 'through process' involving oxidation of isoeugenol followed by subsequent acidic hydrolysis.

Process for preparing methylvanillyl ketone from isoeugenol

The invention relates to the hydrohalide salts of L-.alpha. -methyl-3,4-dihydroxyphenylalanine (methydopa). The method of preparing these and related compounds in the absence of water or other polar solvents is also shown.

Preparation of hydroxyphenylalanine hydrohalide salts

A process for preparing methyl vanillyl ketone from guaiacol is disclosed.

Process for preparing a ketone

A novel improved molecular sieve is prepared by a caustic wash process. The sieves so prepared show improved properties in reactions involving e.g., superior acid scavenging ability.

Caustic washed molecular sieves

This invention relates to the preparation of 3-hydroxymethyl-7.beta.-aminoadipoyl-7.alpha.-methoxy-3-cephem-4-carboxyli c acid from 3-(.alpha.-methoxy-p-sulfo-oxycinnamoyloxymethyl)-7.beta.-aminoadipoyl-7.a lpha.-methoxy-3-cephem-4-carboxylic acid or 3-(.alpha.-methoxy-p-hydroxycinnamoyloxymethyl)-7.beta.-aminoadipoyl-7.alp ha.-methoxy-3-cephem-4-carboxylic acid by treatment at 60.degree. C. and pH 3.5-6.5 for about 1 hour. The starting compounds are isolated as fermentation products produced by various Streptomyces species.

Preparation of

Process for preparing an ester of 3-substituted methyl-7-acylamido-7-methoxy(or hydrogen)-2-cephem-4-carboxylic acid and its corresponding sulfoxide by treating an ester of 3-carbamoyloxymethyl(or 3-lower alkanoyloxymethyl)-7-acylamido-7-methoxy(or hydrogen)-2-cephem-4-carboxyli c acid with a hydrohalic acid or another compound containing an active hydrogen and then with an oxidizing agent. The products obtained are useful as intermediates in the preparation of antibiotics.

3-Substituted methyl-7-acylamino-7-methoxy-2-cephem-4-carboxylic acid

Cephamycin C is concentrated and purified by subjecting a fermentation broth which contains Cephamycin C to the following sequence of steps: filtration at acidic pH, adsorption of filtrate on activated carbon, removing the adsorbed antibiotic by contacting the carbon with a mixture of water and a polar organic solvent, contacting the eluate with an anion exchange resin, and eluting the resin with a salt solution at a pH of from about 5.5 to about 10.

Antibiotic purification process

Process for preparing 5-fluoro-2-methyl-1-(p-methylsulfinylbenzylidene)-indene-3-acetic acid by reacting fluorobenzene with an acid halide, to form an indanone, reaction of the indanone with a methylthio (or methylsulfinyl) benzyl compound to form 5-fluoro-2-methyl-1-(p-methylthiobenzyl) or (p-methylsulfinylbenzyl)-indene and reacting said indene with a glyoxylic acid. This invention relates to new processes for preparing 5-fluoro-2-methyl-1-(p-methylsulfinylbenzylidene)-indene-3-acetic acid, to intermediates thereof and processes for said intermediates.

Process for preparing indene acetic acids

A process for preparing 7-acylamido-7-methoxy-3-substituted methyl-3(or 2)-cephem-4-carboxylic acid and its S-oxide and its salts, esters and amides which comprises treating 7-acylamido-7-methoxy-3-methyl-3(or 2)-cephem-4-carboxylic acid and its S-oxide or the salts or ester derivatives thereof with a reagent capable of replacing a hydrogen atom of the 3-methyl radical with a halo, hydroxy or lower alkanoyloxy radical. The products are either antibiotics or are useful intermediates in the preparation of antibiotics.

Preparation of 7-acylamido-7-methoxy-3-substituted methyl-3(or

Haloalkyl derivatives of aromatic compounds are prepared via reaction with dialkoxy or aralkoxy alkanes in the presence of a Lewis acid.

Chemical compounds and processes

Process for preparing 5-fluoro-2-methyl-1-(p-methylsulfinylbenzylidene)-indene-3-acetic acid by reacting fluorobenzene with an acid halide, to form an indanone, reaction of the indanone with a methylthio (or methylsulfinyl)benzyl compound to form 5-fluoro-2-methyl-1-(p-methylthiobenzyl) or (p-methylsulfinylbenzyl)-indene and reacting said indene with a glyoxylic acid. The invention also relates to intermediates thereof and processes for said intermediates.

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Murray Hill, NJ, United States of America

Seemon H Pines