Process for preparing substituted azetidinones

Details Process for preparing substituted azetidinones Process for preparing substituted azetidinones

1996-10-23

1998-09-15

Berch, Mark L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Unsubstituted hydrocarbyl chain between the ring and the -c-...

549464, C07D40514, C07D40312, C07D20508, C07D31758

Patent

active

058080562

ABSTRACT:
The present invention relates to the process for the preparation of the substituted azetidinone having the formula: ##STR1## comprising a convergent synthesis wherein the azetidinone portion of the molecule is coupled to the lower benzodioxole portion via a base catalyzed addition to an isocyanate.

REFERENCES:
patent: 5149838 (1992-09-01), Humprey et al.
patent: 5348953 (1994-09-01), Doherty et al.
Takahashi, H., et al., "Enantioselective Alkylation of Aldehyde Catalyzed by Disulfonamide-Ti(O-i-Pr)4-Dialkyl Zinc System", Tetrahedron Letters, vol. 30(5), pp. 7095-7098, 1989.
Thompson, A.S., et al., "Direct Conversion of Activated Alcohols to Azides Using Diphenyl Phosphorazidate. A Practical Alternative to Mitsunobu Conditions", J. Org. Chem., vol. 58(22), pp. 5886-5888, 1993.
Dolling, U. H., et al., "Synthesis and Resolution of 3-Fluoro-D,L-Alanine-2-d: A Selective Deuteration via Reductive Amination with Sodium Borodeuteride", J. Org. Chem., vol. 43(9), pp. 1634-1640, 1978.
Berenguer, R., et al., "Enantioselective Reduction of Ketones Catalysed by 1,3,2-Oxazaborolidines Prepared from Phenylglycine", Tetrahedron Asymmetry, vol. 5(2), pp. 165-168, 1994.

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