DK411384A - PROCEDURE FOR THE PREPARATION OF AZETIDINE UNDIVERIVES - Google Patents

PROCEDURE FOR THE PREPARATION OF AZETIDINE UNDIVERIVES Download PDF

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Publication number
DK411384A
DK411384A DK411384A DK411384A DK411384A DK 411384 A DK411384 A DK 411384A DK 411384 A DK411384 A DK 411384A DK 411384 A DK411384 A DK 411384A DK 411384 A DK411384 A DK 411384A
Authority
DK
Denmark
Prior art keywords
lower alkyl
signifies
phenyl
general formula
benzyl
Prior art date
Application number
DK411384A
Other languages
Danish (da)
Other versions
DK411384D0 (en
Inventor
Gerard Schmid
Original Assignee
Hoffmann La Roche
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 Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of DK411384D0 publication Critical patent/DK411384D0/en
Publication of DK411384A publication Critical patent/DK411384A/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic 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
    • C07D405/02Heterocyclic 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
    • C07D405/04Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D205/00Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/06Heterocyclic 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
    • C07D205/08Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D205/00Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/06Heterocyclic 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
    • C07D205/08Heterocyclic 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
    • C07D205/085Heterocyclic 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 nitrogen atom directly attached in position 3
    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/55Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

1. A process for the manufacture of optically uniform azetidinones of the general formula see diagramm : EP0138113,P5,F1 wherein R signifies benzyl, beta-(trimethylsilyl)-lower alkyl or beta-halo-lower alkyl, R**1 signifies a readily cleavable protecting group from the group consisting of benzyl, 2,4- or 3,4-di(lower alkoxy)benzyl, di[4-(lower alkoxy)phenyl]methyl, 4-(lower alkoxy)phenyl, lower 2-alkenyl and the group of the formula -CH2 -CH(OR**5)2 (a) or see diagramm : EP0138113,P5,F2 in which R**5 signifies lower alkyl and n signifies the number 0 or 1, R**2 signifies lower alkyl, phenyl-lower alkyl or lower alkoxyalkyl and R**3 signifies lower alkyl or phenyl-lower alkyl or R**2 and R**3 together with the centre of chirality and the oxygen atom signify a 5 or 6-membered 0-heterocycle which optionally contains a further oxygen atom not directly linked with the centre of chirality and which is optionally substituted by lower alkyl, lower alkoxy, oxo or spirocyclo-lower alkyl, and the residues denoted by lower have up to eight carbon atoms, characterized by reacting an alkali metal salt of a carboxylic acid of the general formula ROCONHCH2 COOH wherein R has the above significance, with an optically uniform compound of the general formula see diagramm : EP0138113,P6,F3 wherein R**1, R**2 and R**3 have the above significance, in the presence of a base and a sulphonic acid chloride of the general formula R**4-SO2 -Cl wherein R**4 signifies phenyl, lower alkylphenyl, halophenyl, lower alkyl or halo-lower alkyl, whereby the reaction is carried out in an anhydrous inert organic solvent at a temperature in the range of about -30 degrees C to about 50 degrees C.
DK411384A 1983-10-03 1984-08-28 PROCEDURE FOR THE PREPARATION OF AZETIDINE UNDIVERIVES DK411384A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH536583 1983-10-03

Publications (2)

Publication Number Publication Date
DK411384D0 DK411384D0 (en) 1984-08-28
DK411384A true DK411384A (en) 1985-04-04

Family

ID=4292341

Family Applications (1)

Application Number Title Priority Date Filing Date
DK411384A DK411384A (en) 1983-10-03 1984-08-28 PROCEDURE FOR THE PREPARATION OF AZETIDINE UNDIVERIVES

Country Status (13)

Country Link
EP (1) EP0138113B1 (en)
JP (1) JPS6092263A (en)
KR (1) KR850003392A (en)
CN (1) CN85100624A (en)
AT (1) ATE33830T1 (en)
AU (1) AU572194B2 (en)
CA (1) CA1251455A (en)
DE (1) DE3470736D1 (en)
DK (1) DK411384A (en)
IL (1) IL73089A (en)
NZ (1) NZ209684A (en)
PH (1) PH19418A (en)
ZA (1) ZA847585B (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60139667A (en) * 1983-12-27 1985-07-24 Takeda Chem Ind Ltd Preparation of azetidinone
US5142039A (en) * 1987-07-31 1992-08-25 Eli Lilly And Company β-lactam antibiotics
ATE88186T1 (en) * 1987-07-31 1993-04-15 Lilly Co Eli METHOD OF DEPROTECTING 3AMINOAZETIDINONES.
US4983732A (en) * 1987-07-31 1991-01-08 Eli Lilly And Company Method of deprotection of 3-amino azetidinones
US5239068A (en) * 1987-07-31 1993-08-24 Eli Lilly And Company Bicyclic β-lactam antibiotics
CN112175173B (en) * 2020-10-09 2022-04-19 中国科学技术大学 Preparation method of degradable poly-alpha-olefin material with controllable olefin insertion rate

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1262128A (en) * 1981-08-27 1989-10-03 Christian N. Hubschwerlen .beta.-lactams
CA1251454A (en) * 1983-01-20 1989-03-21 Gerard Schmid PROCESS FOR THE MANUFACTURE OF .beta.-LACTAMES
DK36784A (en) * 1983-02-25 1984-08-26 Hoffmann La Roche PROCEDURE FOR PREPARING CHIRAL ALDEHYDES
JPS60139667A (en) * 1983-12-27 1985-07-24 Takeda Chem Ind Ltd Preparation of azetidinone

Also Published As

Publication number Publication date
CA1251455A (en) 1989-03-21
IL73089A0 (en) 1984-12-31
AU572194B2 (en) 1988-05-05
EP0138113B1 (en) 1988-04-27
ATE33830T1 (en) 1988-05-15
DK411384D0 (en) 1984-08-28
JPS6092263A (en) 1985-05-23
AU3370584A (en) 1985-04-18
EP0138113A1 (en) 1985-04-24
NZ209684A (en) 1987-08-31
ZA847585B (en) 1985-05-29
DE3470736D1 (en) 1988-06-01
KR850003392A (en) 1985-06-17
IL73089A (en) 1988-02-29
CN85100624A (en) 1986-07-09
PH19418A (en) 1986-04-10

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Legal Events

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AHS Application shelved for other reasons than non-payment
AHS Application shelved for other reasons than non-payment