GB841915A - Azetidinones and the preparation thereof - Google Patents

Azetidinones and the preparation thereof

Info

Publication number
GB841915A
GB841915A GB3852257A GB3852257A GB841915A GB 841915 A GB841915 A GB 841915A GB 3852257 A GB3852257 A GB 3852257A GB 3852257 A GB3852257 A GB 3852257A GB 841915 A GB841915 A GB 841915A
Authority
GB
United Kingdom
Prior art keywords
phenyl
hydrogen
alpha
ethyl
compounds
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
Application number
GB3852257A
Inventor
Emilio Testa
Luigi Fontanella
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.)
Gruppo Lepetit SpA
Original Assignee
Lepetit SpA
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 Lepetit SpA filed Critical Lepetit SpA
Priority to GB3852257A priority Critical patent/GB841915A/en
Priority to CH5895258A priority patent/CH395101A/en
Priority to CH314463A priority patent/CH425800A/en
Publication of GB841915A publication Critical patent/GB841915A/en
Expired legal-status Critical Current

Links

Classifications

    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises compounds of the general formula <FORM:0841915/IV(b)/1> wherein R and R1 are the same or different and represent alkyl radicals containing at most 8 carbon atoms or dialkylaminoalkyl, aryl, aralkyl or cycloalkyl radicals and R2 is hydrogen or an alkyl radical of at most 8 carbon atoms, provided that one of R1 and R2 is a dialkylaminoalkyl radical when R2 is hydrogen; and the preparation of all the above compounds and of the compounds claimed in Specification 829,663 by reacting one mole of an amino ester of the formula <FORM:0841915/IV(b)/2> with two to four moles of an alkyl magnesium halide in an anhydrous organic solvent such as benzene or ether or mixtures thereof at a temperature between 0 DEG and 5 DEG C. for one to eight hours. Examples describe the preparation of compounds of the above general formula wherein R, R1 and R2 have the following values : .R.R1.R2 .phenyl.ethyl.hydrogen .phenyl.n-propyl.hydrogen .phenyl.iso-propyl.hydrogen .ethyl.ethyl.hydrogen .phenyl.phenyl.hydrogen .phenyl.methyl.hydrogen .phenyl.iso-butyl.hydrogen .phenyl.cyclohexyl.hydrogen .phenyl.benzyl.hydrogen .ethyl.benzyl.hydrogen .phenyl.3-(dimethyl-.hydrogen ..lamino)-propyl.hydrogen .phenyl.ethyl.methyl The optically active isomers of the first of the above named compounds are also prepared from the optical antipodes of ethyl alpha-phenyl alpha-aminomethyl butyrate, these being prepared by resolution of the DL-compound using D-dibenzoyl tartaric acid. Ethyl alpha - phenyl - alpha - methylamino-methyl butyrate is prepared by methylation of ethyl alpha-phenyl-alpha-aminomethyl butyrate with formic acid and formaldehyde. Ethyl alpha - aminomethyl - alpha - phenyl-delta-dimethylaminovalerate is prepared by condensing ethyl alpha-cyano-alpha-phenyl acetate with 3-dimethylamino-1-chloro-propane and reducing the ethyl alpha-cyano-alpha-phenyl-delta-dimethylaminovalerate so formed.
GB3852257A 1957-05-06 1957-12-11 Azetidinones and the preparation thereof Expired GB841915A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
GB3852257A GB841915A (en) 1957-12-11 1957-12-11 Azetidinones and the preparation thereof
CH5895258A CH395101A (en) 1957-05-06 1958-04-30 Process for the preparation of 3,3-disubstituted azetidinones- (2)
CH314463A CH425800A (en) 1957-05-06 1958-04-30 Process for the preparation of new 3,3-disubstituted azetidinones- (2)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3852257A GB841915A (en) 1957-12-11 1957-12-11 Azetidinones and the preparation thereof

Publications (1)

Publication Number Publication Date
GB841915A true GB841915A (en) 1960-07-20

Family

ID=10404031

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3852257A Expired GB841915A (en) 1957-05-06 1957-12-11 Azetidinones and the preparation thereof

Country Status (1)

Country Link
GB (1) GB841915A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1987004429A1 (en) * 1986-01-23 1987-07-30 The Upjohn Company Antimicrobial n-acyl-2-azetidinones

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1987004429A1 (en) * 1986-01-23 1987-07-30 The Upjohn Company Antimicrobial n-acyl-2-azetidinones
EP0232017A1 (en) * 1986-01-23 1987-08-12 The Upjohn Company Antimicrobial N-acyl-2-azetidinones

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