Process for preparation of 3-exomethylene cepham sulfoxide ester

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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C07D50102

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active

055787215

ABSTRACT:
A process for the manufacture of 3-exomethylene cepham sulfoxide ester of the formula ##STR1## wherein R is hydrogen, C.sub.1 -C.sub.3 alkyl, halomethyl, phenyl, substituted phenyl cyanomethyl, phenoxy, benzyloxy or substituted benzyl with a substituent group such as that selected from halo, alkyl, alkoxy, protected hydroxy, nitro, cyano and trifiuoromethyl, a group of the formula R.sub.2 --0-- wherein R.sub.2 is t-butyl, 2,2,2-trichloro ethyl, benzyl or substituted benzyl; a group of the formula R.sub.3 --[0].sub.n --CH.sub.2, wherein R.sub.3 is phenyl or substituted phenyl with the substituent group selected from halo, alkyl, alkoxy, protected hydroxy, nitro, cyano, or 1,4-cyclohexadienyl, and n is 0 or 1; or a substituted arylalkyl group of formula R.sub.4 --CH where R.sub.4 has the same meaning as R.sub.3 defined above and W is a protected hydroxy or protected amino group; and R.sub.1 is a carboxylic acid protecting group such as that selected from the group consisting of C.sub.1 -C.sub.4 alkyl, 2,2,2-trihalo alkyl, benzyl, substituted benzyl such as para nitrobenzyl, phenacyl, halo substituted phenacyl and benzhydryl is disclosed. Such compound is prepared by reacting a chlorosulfinylazetidinone of the formula ##STR2## wherein R and R.sub.1 have the same meanings as defined above, with a Lewis Acid type Friedel-Crafts catalyst and a sulfur compound in an inert solvent under anhydrous condition. These compounds find application as an intermediate for the preparation of cephalosporin antibiotics.

REFERENCES:
patent: Re31730 (1984-11-01), Bouzard
patent: Re33948 (1992-06-01), Schmidt
patent: 3641014 (1972-02-01), Murphy
patent: 3665003 (1972-05-01), Kennedy
patent: 3668201 (1972-06-01), Gutowski
patent: 3668202 (1972-06-01), Foster
patent: 3668203 (1972-06-01), Clark
patent: 3716533 (1973-02-01), Humber
patent: 3769277 (1973-10-01), Long
patent: 3775408 (1973-11-01), Ochial
patent: 3792995 (1974-02-01), Ochial
patent: 3883518 (1975-05-01), Ponticello
patent: 3917587 (1975-11-01), Chauvette
patent: 3917588 (1975-11-01), Chauvette
patent: 3925372 (1975-12-01), Chauvette
patent: 3932392 (1976-01-01), Johnson
patent: 3932393 (1976-01-01), Chauvette
patent: 3989695 (1976-11-01), Scartazzini
patent: 4031084 (1977-06-01), Kukolja
patent: 4048162 (1977-09-01), Kukolja
patent: 4052387 (1977-10-01), Kukolja
patent: 4060688 (1977-11-01), Chauvette
patent: 4064343 (1977-12-01), Chauvette
patent: 4068071 (1978-01-01), Tsushima
patent: 4068072 (1978-01-01), Tsushima
patent: 4075203 (1978-02-01), Chou
patent: 4081440 (1978-03-01), Kukolja
patent: 4113940 (1978-09-01), Kamiya
patent: 4115643 (1978-09-01), Kukolja
patent: 4123612 (1978-10-01), Gorman
patent: 4147864 (1979-04-01), Woodward
patent: 4159272 (1979-06-01), Chou
patent: 4160085 (1979-07-01), Tsuji
patent: 4160091 (1979-07-01), Herron
patent: 4165315 (1979-08-01), Kukolja
patent: 4165316 (1979-08-01), Chou
patent: 4176231 (1979-11-01), Corfield
patent: 4178445 (1979-12-01), Takano
patent: 4182870 (1980-01-01), Bruynes
patent: 4190724 (1980-02-01), Chou
patent: 4208515 (1980-06-01), Chauvette
patent: 4211702 (1980-09-01), Hatfield
patent: 4223133 (1980-09-01), Bunnell
patent: 4226986 (1980-10-01), Hatfield
patent: 4230620 (1980-10-01), Chou
patent: 4240988 (1980-12-01), Bingham, Jr.
patent: 4252950 (1981-02-01), Chauvette
patent: 4252973 (1981-02-01), Slusarchyk
patent: 4254029 (1981-03-01), Kaspi
patent: 4255328 (1981-03-01), Woodward
patent: 4260745 (1981-04-01), Chauvette
patent: 4271305 (1981-06-01), Hatfield
patent: 4275062 (1981-06-01), Breuer
patent: 4281116 (1981-07-01), Chauvette
patent: 4281117 (1981-07-01), Chauvette
patent: 4289695 (1981-09-01), Chou
patent: 4301278 (1981-11-01), Woodward
patent: 4301279 (1981-11-01), Scartazzini
patent: 4301280 (1981-11-01), Corfield
patent: 4304718 (1981-12-01), Kamiya
patent: 4310459 (1982-01-01), Cundall
patent: 4316955 (1982-02-01), Abbott
patent: 4319027 (1982-03-01), Woodward
patent: 4322347 (1982-03-01), Cundall
patent: 4332722 (1982-06-01), Tsuji
patent: 4334063 (1982-06-01), Spry
patent: 4336191 (1982-06-01), Kukolja
patent: 4338436 (1982-07-01), Herron
patent: 4346218 (1982-08-01), Tsuji
patent: 4354022 (1982-10-01), Takaya
patent: 4363807 (1982-12-01), Takaya
patent: 4366315 (1982-12-01), Bruynes
patent: 4368156 (1983-01-01), Spitzer
patent: 4368325 (1983-01-01), Ueda
patent: 4374982 (1983-02-01), Cundall
patent: 4385176 (1983-05-01), Kamiya
patent: 4389524 (1983-06-01), Scartazzini
patent: 4405782 (1983-09-01), Palomo-Coll
patent: 4410458 (1983-10-01), Kamiya
patent: 4431803 (1984-02-01), Kukolja
patent: 4477658 (1984-10-01), Scartazzini
patent: 4499265 (1985-02-01), Torii
patent: 4513134 (1985-04-01), Kim
patent: 4515719 (1985-05-01), McShane
patent: 4518773 (1985-05-01), Cundall
patent: 4558123 (1985-12-01), McShane
patent: 4562253 (1985-12-01), Prager
patent: 4591642 (1986-05-01), Scartazzini
patent: 4623645 (1986-11-01), Doherty
patent: 4629542 (1986-12-01), Torii
patent: 4668781 (1987-05-01), Scartazzini
patent: 4695627 (1987-09-01), Verweij
patent: 4716227 (1987-12-01), Furlenmeier
patent: 4767851 (1988-08-01), Palomo-Coll
patent: 4853468 (1989-08-01), Torii
patent: 4855418 (1989-08-01), Cook
patent: 4888100 (1989-12-01), Hertel
patent: 4921954 (1990-05-01), Witkamp
patent: 4927818 (1990-05-01), Takaya
patent: 4950753 (1990-08-01), Copp
patent: 4958018 (1990-09-01), Torii
patent: 4968508 (1990-11-01), Oren
patent: 4985554 (1991-01-01), Verweij
patent: 4994454 (1991-02-01), Verweij
patent: 5015725 (1991-05-01), Scoggins
patent: 5051406 (1991-09-01), Satoh
patent: 5053501 (1991-10-01), Kapur
patent: 5066797 (1991-11-01), Baldwin
patent: 5070195 (1991-12-01), Khanna
patent: 5095107 (1992-03-01), Blanchard
patent: 5109132 (1992-04-01), Verweij
patent: 5126446 (1992-06-01), Brown
patent: 5132419 (1992-07-01), Lanz
patent: 5142043 (1992-08-01), Schreiber
patent: 5159071 (1992-10-01), Khanna
patent: 5162522 (1992-10-01), Naito
patent: 5204458 (1993-04-01), Torii
patent: 5229509 (1993-07-01), Nieves Elvira
patent: 5246926 (1993-09-01), Bateson
patent: 5250525 (1993-10-01), Kovacevic
patent: 5254680 (1993-10-01), Alpegiani
patent: 5302713 (1994-04-01), Yeh
patent: 5347000 (1994-09-01), Khanna
patent: 5350845 (1994-09-01), Brown, Jr.

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