N-(substituted-methyl)-azetidin-2-ones

Details N-(substituted-methyl)-azetidin-2-ones N-(substituted-methyl)-azetidin-2-ones

1985-04-01

1986-06-17

Berch, Mark L.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2602454, 2603303, 2603309, 544316, 544359, 546275, 548231, C07D20508, C07D41304, C07D40304, C07D40112

Patent

active

045955328

ABSTRACT:
N-Mono or N-disubstituted methyl-2-azetidinones are provided via cyclization of .beta.-hydroxy or .beta.-halo substituted acid sec-amides wherein the amide nitrogen is substituted with a mono- or di-substituted methyl group having activating substituents. Cyclization of .beta.-hydroxy acid amides is mediated by triphenylphosphine-dialkylazodicarboxylate while cyclization of .beta.-halo acid amides is mediated by strong bases e.g. lithium dialkylamides. E.g. Diethyl amino-protected L-serylaminomalonate is cyclized with 200 mole % TPP-diisopropylazodicarboxylate to N-(diethoxycarbonylmethyl)-3-protected-amino-2-azetidinone. The 2-azetidinones provided are useful intermediates.

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