AU2474584A - Process for the manufacture of chiral beta-lactams - Google Patents

Process for the manufacture of chiral beta-lactams

Info

Publication number
AU2474584A
AU2474584A AU24745/84A AU2474584A AU2474584A AU 2474584 A AU2474584 A AU 2474584A AU 24745/84 A AU24745/84 A AU 24745/84A AU 2474584 A AU2474584 A AU 2474584A AU 2474584 A AU2474584 A AU 2474584A
Authority
AU
Australia
Prior art keywords
general formula
above significance
see diagramm
formula see
reacting
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.)
Granted
Application number
AU24745/84A
Other versions
AU570032B2 (en
Inventor
Christian Nicolas Hubschwerlen
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of AU2474584A publication Critical patent/AU2474584A/en
Application granted granted Critical
Publication of AU570032B2 publication Critical patent/AU570032B2/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen 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
    • C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen 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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/32—Oxygen atoms
    • C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
    • C07D317/20—Free hydroxyl or mercaptan
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/26—Radicals substituted by doubly bound oxygen or sulfur atoms or by two such atoms singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/28—Radicals substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Cephalosporin Compounds (AREA)
  • Pyrrole Compounds (AREA)

Abstract

1. A process for the manufacture of chiral beta-lactams of the general formula see diagramm : EP0120289,P14,F1 wherein R**1 signifies a readily cleavable protecting group, R**2 signifies azido, phthalimido or the group ROCO-CH=C(CH3 )-NH-, R signifies lower alkyl and R**3 and R**4 each individually signify hydrogen or lower alkyl or together signify alkylene with a maximum of 6 carbon atoms, and the groups denoted by lower have a maximum of 4 carbon atoms, characterized by reacting a lactone of the general formula see diagramm : EP0120289,P14,F2 wherein R**3 and R**4 have the above significance, with an alkali metal periodate, reacting the resulting aldehyde of the general formula see diagramm : EP0120289,P14,F3 wherein R**3 and R**4 have the above significance, with an amine of the general formula H2 N-R**1 wherein R**1 has the above significance, and reacting the thus-obtained compound of the general formula see diagramm : EP0120289,P14,F4 wherein R**1, R**3 and R**4 have the above significance, in the presence of a base with a reactive derivative of a carboxylic acid of the general formula R**2-CH2 -COOH wherein R**2 has the above significance.
AU24745/84A 1983-02-25 1984-02-20 Process for the manufacture of chiral beta-lactams Ceased AU570032B2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
CH106183 1983-02-25
CH1061/83 1983-02-25
CH3384 1984-01-05
CH33/84 1984-01-05

Publications (2)

Publication Number Publication Date
AU2474584A true AU2474584A (en) 1984-08-30
AU570032B2 AU570032B2 (en) 1988-03-03

Family

ID=25683311

Family Applications (1)

Application Number Title Priority Date Filing Date
AU24745/84A Ceased AU570032B2 (en) 1983-02-25 1984-02-20 Process for the manufacture of chiral beta-lactams

Country Status (9)

Country Link
EP (1) EP0120289B1 (en)
AT (1) ATE34389T1 (en)
AU (1) AU570032B2 (en)
CA (1) CA1224789A (en)
DE (1) DE3471306D1 (en)
DK (1) DK36784A (en)
IL (1) IL71006A (en)
NZ (1) NZ207193A (en)
PH (1) PH20100A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU566914B2 (en) * 1983-01-20 1987-11-05 F. Hoffmann-La Roche & Co. Manufacture of beta-lactams
AU572194B2 (en) * 1983-10-03 1988-05-05 F. Hoffmann-La Roche Ag Azetidinone derivatives

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2061736A1 (en) * 1991-02-28 1992-08-29 Christopher Randall Schmid Glyceraldehyde-3-pentanide and process for producing same
CA2877026A1 (en) 2012-05-18 2013-11-21 Amgen Inc. Method for the preparation of thiadiazoles

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2541438A1 (en) * 1975-09-17 1977-03-31 Basf Ag Odoriferous dioxolane aldehydes prepn. - by hydroformation of vinyl dioxolanes; for detergents, perfumes, soaps, etc.
US4111958A (en) * 1977-06-03 1978-09-05 Pfizer Inc. Ascorbic acid synthesis
CA1262128A (en) * 1981-08-27 1989-10-03 Christian N. Hubschwerlen .beta.-lactams
EP0096296B1 (en) * 1982-06-03 1987-07-29 F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft 1-sulfo-2-oxoazetidine derivatives
CA1204746A (en) * 1982-08-19 1986-05-20 Hoffmann-La Roche Limited .beta. LACTAMS
CA1251454A (en) * 1983-01-20 1989-03-21 Gerard Schmid PROCESS FOR THE MANUFACTURE OF .beta.-LACTAMES

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU566914B2 (en) * 1983-01-20 1987-11-05 F. Hoffmann-La Roche & Co. Manufacture of beta-lactams
AU572194B2 (en) * 1983-10-03 1988-05-05 F. Hoffmann-La Roche Ag Azetidinone derivatives

Also Published As

Publication number Publication date
DK36784A (en) 1984-08-26
IL71006A0 (en) 1984-05-31
CA1224789A (en) 1987-07-28
IL71006A (en) 1988-10-31
EP0120289A3 (en) 1985-01-23
AU570032B2 (en) 1988-03-03
EP0120289B1 (en) 1988-05-18
PH20100A (en) 1986-09-24
NZ207193A (en) 1987-10-30
DK36784D0 (en) 1984-01-26
EP0120289A2 (en) 1984-10-03
ATE34389T1 (en) 1988-06-15
DE3471306D1 (en) 1988-06-23

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