Process for synthesizing carbapenem intermediates

Details Process for synthesizing carbapenem intermediates Process for synthesizing carbapenem intermediates

1998-07-27

2000-06-27

Berch, Mark L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D20508

Patent

active

060808543

ABSTRACT:
A process of synthesizing a compound of formula I is described: ##STR1## wherein P and P' independently represent H or a protecting group, R.sub.1 represents H or C.sub.1-4 alkyl, and Hal represents a halogen characterized by reacting a compound of formula 2: ##STR2## with R.sub.2 OH, wherein R.sub.2 is C.sub.1-4 alkyl, C.sub.6-10 aryl or C.sub.5-10 heteroaryl in the presence of an acid catalyst or carbodiimide reagent to produce a compound of formula 3: ##STR3## and reacting a compound of formula 3 in the presence of a base and a haloalkylating agent to produce a compound of formula 1.

REFERENCES:
Shiozaki, Tetrahedron 40(10) 1795, 1984.
S. M. Schmitt et al. J. Antibiotic, 41(6), p. 780-787 (1988).

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