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US 6,617,451 B1Granted
Enantioselective acylation of cis racemic azetidinones
AssigneeEli Lilly and Company
InventorsKathy Sue Crichfield, John Eric Hart, Radhe Krishan Vaid, Daniel Edward Verral
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Abstract
Cis-β-lactam compounds having structure (II) are described herein which are prepared by enantioselective acylation of the free amine in the presence of Penicillin G Amidase.
Claims4
A process for preparing a cis-β-lactam having structure II
- where R1 is —SO3(C1-C4)alkyl, —CH2CO2H, or —CH2CO2R1′, where R1′ is (C1-C4)alkyl, benzyl, or p-nitrophenylmethylene;
- R2 is benzyl or phenoxymethylene;
- and R3 is 2-furyl, phenyl, or 2-methoxyphenyl comprising the steps of
- (i) providing a racemic mixture of cis-azetidinones having structures Ia and Ib where R1 is —SO3(C1-C4)alkyl, —CH2CO2H, or —CH2CO2R1′, where R1 is (C1-C4)alkyl, benzyl, or p-nitrophenylmethylene and R3 is 2-furyl, phenyl, or 2-methoxyphenyl;
- and
- (ii) reacting said racemic mixture with a (C1-C4)alkyl phenylacetate or a (C1-C4)alkyl phenoxyacetate in the presence of penicillin G amidase.
3 more elements
A process for preparing a cis-β-lactam having structure III
- where R1 is —SO3(C1-C4)alkyl, —CH2CO2H, or —CH2CO2R1′, where R1 is (C1-C4)alkyl, benzyl, or p-nitrophenylmethylene;
- R2 is benzyl or phenoxymethylene;
- and R3 is 2-furyl, phenyl, or 2-methoxyphenyl comprising the steps of
- (i) providing a racemic mixture of cis-azetidinones having structures Ia and Ib
- where R1 is —SO3(C1-C4)alkyl, —CH2CO2H, or —CH2CO2R1′, where R1′ is (C1-C4)alkyl, benzyl, or p-nitrophenylmethylene;
- and R3 is 2-furyl, phenyl, or 2-methoxyphenyl;
- and
- (ii) reacting said racemic mixture with a (C1-C4)alkyl phenylacetate or a (C1-C4)alkyl phenoxyacetate in the presence of penicillin G amidase to produce a cis-β-lactam having structure II
- where R1 is —SO3(C1-C4)alkyl, —CH2CO2H, or —CH2CO2R1′, where R1′ is (C1-C4)alkyl, benzyl, or p-nitrophenylmethylene;
- R2 is benzyl or phenoxymethylene;
- and R3 is 2-furyl, phenyl, or 2-methoxyphenyl;
- and
- (iii) hydrogenating said cis-β-lactam having structure II to produce said cis-β-lactam having structure III.
10 more elements
Dependencies are inferred from the claim text.