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- Inventor(s):
- Min Teng, Marvin J. Miller
- Patent Number:
- US 5750681 B2
- Description:
Bicyclic .beta.-lactams comprising a 5- or 6-membered lactone or lactam ring are obtained in a process comprising a base induced intramolecular cyclization of a 4-substututed .beta.-lactam having a leaving group in the 1-position. An intramolecular nucleophile transfer reaction is proposed as the operative mechanism and the bicyclic .beta.-lactams are obtained in the required stereochemical form for biological activity. The compounds provided are useful intermediates for the preparation of an…
- Date Issued:
- 1998-05-12
- Record Visibility:
- Public
- Title
- Bicyclic beta-lactams and process therefor
- Description
- Bicyclic .beta.-lactams comprising a 5- or 6-membered lactone or lactam ring are obtained in a process comprising a base induced intramolecular cyclization of a 4-substututed .beta.-lactam having a leaving group in the 1-position. An intramolecular nucleophile transfer reaction is proposed as the operative mechanism and the bicyclic .beta.-lactams are obtained in the required stereochemical form for biological activity. The compounds provided are useful intermediates for the preparation of antibiotics and .beta.-lactamase inhibitors.
- Creator
- Min Teng, Marvin J. Miller
- Publisher
- United States Patent and Trademark Office
- Language
- eng
- Rights
- http://creativecommons.org/publicdomain/zero/1.0/
- Resource Type
- Patent
-
- 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