Process for synthesizing carbapenem antibiotics

Details Process for synthesizing carbapenem antibiotics Process for synthesizing carbapenem antibiotics

1997-07-30

1999-02-16

Berch, Mark L.

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

Organic compounds

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

548556, C07D47720, C07D20716

Patent

active

058722505

ABSTRACT:
A process for synthesizing a compound of the formula I: ##STR1## or a pharmaceutically acceptable salt or ester thereof, wherein each P independently represents H or a protecting group, and R.sup.1 and R.sup.2 independently represent H, C.sub.1-10 alkyl, aryl or heteroaryl, or substituted C.sub.1-10 alkyl, aryl or heteroaryl, comprising:
reacting the compounds: ##STR2## or a pharmaceutically acceptable salt or ester thereof, and ##STR3## or a pharmaceutically acceptable salt or ester thereof, wherein X represents OP(O)(OR).sub.2, or OSO.sub.2 R, wherein R represents C.sub.1-6 alkyl, aryl or perfluoro C.sub.1-6 alkyl, in the presence of an amine selected from the group consisting of: diisopropylamine (DIPA), dicyclohexylamine (DCHA), 2,2,6,6-tetramethylpiperidine (TMP), formula I.

REFERENCES:
M. Sunagawa et al., J. Antibiotic, 44(4) pp. 459-462, 1991.
M. Sunagawa et al., J. Antibiotic, 43(5) pp. 519-532, 1990.

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