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    Patent

    Process for the preparation of 3-substituted-2-azetidinones
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    Inventor(s):
    Catherine M. Gasparski, Marvin J. Miller, Min Teng
    Patent Number:
    US 5250676 B2
    Description:

    Provided is a process for diastereoselectively preparing compounds of the formula ##STR1## which includes the step of subjecting a compound of the formula ##STR2## to a salt whose anion is a nucleophilic base whose conjugate acid has a pKa in the range of between about -7 to about 14, or a silylated derivative of the salt; wherein R.sub.1 is said nucleophile; R is hydrogen, or protected amino, R.sub.2 is R.sub.4 as defined herein below; R.sub.3 is a leaving group; and R.sub.4 is hydrogen, C.s…

    Date Issued:
    1993-10-05
    Record Visibility:
    Public
    Title
    Process for the preparation of 3-substituted-2-azetidinones
    Description
    Provided is a process for diastereoselectively preparing compounds of the formula ##STR1## which includes the step of subjecting a compound of the formula ##STR2## to a salt whose anion is a nucleophilic base whose conjugate acid has a pKa in the range of between about -7 to about 14, or a silylated derivative of the salt; wherein R.sub.1 is said nucleophile; R is hydrogen, or protected amino, R.sub.2 is R.sub.4 as defined herein below; R.sub.3 is a leaving group; and R.sub.4 is hydrogen, C.sub.1 -C.sub.6 alkyl, or a group of the formula wherein R.sub.6 is 2-furyl, naphthyl, phenyl, phenyl substituted with 1, 2 or 3 substituents selected from C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, nitro, halo, carboxy and amido; or R.sub.6 is a group of the formula in which R.sub.7 is selected from C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, benzyl, phenyl, or benzyl or phenyl substituted with 1, 2 or 3 substituents selected from C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, nitro, halo, carboxy and amido; or R.sub.4 is a group of the formula ##STR3## wherein L is --OR.sub.7 where R.sub.7 is as defined; or R.sub.4 is a group of the formula ##STR4## wherein: G is trimethylsilylmethyl, hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 substituted alkyl, phenyl, or phenyl substituted with 1, 2 or 3 substituents selected from C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, nitro, halo, carboxy and amido.
    Creator
    Catherine M. Gasparski, Marvin J. Miller, Min Teng
    Publisher
    United States Patent and Trademark Office
    Language
    eng
    Rights
    http://creativecommons.org/publicdomain/zero/1.0/
    Resource Type
    Patent
1 entry found