CA1299172C - Synthesis of azetidinones - Google Patents

Synthesis of azetidinones

Info

Publication number
CA1299172C
CA1299172C CA000542505A CA542505A CA1299172C CA 1299172 C CA1299172 C CA 1299172C CA 000542505 A CA000542505 A CA 000542505A CA 542505 A CA542505 A CA 542505A CA 1299172 C CA1299172 C CA 1299172C
Authority
CA
Canada
Prior art keywords
compound
formula
protecting group
reaction
product
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
CA000542505A
Other languages
English (en)
French (fr)
Inventor
Donald C. Hou
Martin Steinman
Yee-Shing Wong
Dinesh Gala
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck Sharp and Dohme LLC
Original Assignee
Schering Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Schering Corp filed Critical Schering Corp
Application granted granted Critical
Publication of CA1299172C publication Critical patent/CA1299172C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D499/88—Compounds with a double bond between positions 2 and 3 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
    • C07D205/09—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CA000542505A 1986-07-21 1987-07-20 Synthesis of azetidinones Expired - Lifetime CA1299172C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US06/887,394 US4767853A (en) 1986-07-21 1986-07-21 Synthesis of 1-(allyloxycarbonyl)-methyl-3-(hydroxyethyl)-4-beta-naphthoxythiocarbonylthio-2-azetidinones and hydroxy protected analogs thereof
US887,394 1986-07-21

Publications (1)

Publication Number Publication Date
CA1299172C true CA1299172C (en) 1992-04-21

Family

ID=25391044

Family Applications (1)

Application Number Title Priority Date Filing Date
CA000542505A Expired - Lifetime CA1299172C (en) 1986-07-21 1987-07-20 Synthesis of azetidinones

Country Status (8)

Country Link
US (1) US4767853A (OSRAM)
EP (1) EP0255278B1 (OSRAM)
JP (1) JPS6333360A (OSRAM)
AT (1) ATE73456T1 (OSRAM)
CA (1) CA1299172C (OSRAM)
DE (1) DE3777274D1 (OSRAM)
ES (1) ES2033313T3 (OSRAM)
GR (1) GR3004216T3 (OSRAM)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4119856A1 (de) * 1991-06-17 1992-12-24 Hoechst Ag N-acyl-s-(2-hydroxyalkyl)-cysteine, deren herstellung sowie deren verwendung als zwischenprodukte zur herstellung von synthetischen immunadjuvantien und synthetischen impfstoffen
GB0124574D0 (en) 2001-10-12 2001-12-05 Biogemma Uk Ltd Oil biosynthesis
CA2839570C (en) 2011-06-23 2020-04-07 Rho Renewables, Inc. Recombinant production systems for decarboxylated aromatic molecules

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3311638A (en) * 1961-08-16 1967-03-28 Bristol Myers Co Anhydropenicillins
US3948927A (en) * 1972-04-10 1976-04-06 Queen's University 2,2-Dimethyl-3R-carboxy-6S-amino-1-oxa-4-aza-5R-bicyclo-[3,2,0]heptan-7-one
US4347183A (en) * 1981-02-02 1982-08-31 Schering Corporation Process for the synthesis of penems and carbapenems
US4411906A (en) * 1981-11-25 1983-10-25 Schering Corporation (5R,6S,8R)-6-(1-Hydroxyethyl)-2-(2-fluoroethylthio)-penem-3-carboxylates
US4443373A (en) * 1982-03-30 1984-04-17 Schering Corporation Process for the production of antibiotic penems
DE3382761T2 (de) * 1982-11-29 1995-03-09 Schering Corp Verfahren zur Herstellung von Penem-Verbindungen.
US4530793A (en) * 1982-11-29 1985-07-23 Schering Corporation Processes for the production of penems
EP0115308A3 (en) * 1983-01-25 1984-10-10 Merck & Co. Inc. 2-unsaturated alkylthio-pen-2-em-3-carboxylic acids and process for preparing substituted 2-thioxopenams and 2-substituted thiopenems
US4584133A (en) * 1983-11-07 1986-04-22 Schering Corporation Process for the production of penems
US4559333A (en) * 1984-03-01 1985-12-17 Schering Corporation Hydrazone substituted penems
US4596677A (en) * 1984-04-06 1986-06-24 Bristol-Myers Company Anhydropenicillin intermediates

Also Published As

Publication number Publication date
GR3004216T3 (OSRAM) 1993-03-31
JPS6333360A (ja) 1988-02-13
ES2033313T3 (es) 1993-03-16
EP0255278B1 (en) 1992-03-11
DE3777274D1 (de) 1992-04-16
ATE73456T1 (de) 1992-03-15
US4767853A (en) 1988-08-30
EP0255278A1 (en) 1988-02-03

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