Process for 2-(aminoalkylthio) carbapenems

Details Process for 2-(aminoalkylthio) carbapenems Process for 2-(aminoalkylthio) carbapenems

1987-05-11

1990-01-16

Gerstl, Robert

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

Organic compounds

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

C07D48704

Patent

active

048944505

ABSTRACT:
This invention relates to a process for preparing 2-(aminoalkylthio)carbapenems. In particular, this invention relates to a process in which a bis(substituted phenyl) phosphorohalidate is used to form an enol phosphate intermediate that can be converted to 2-(aminoalkylthio)carbapenems by reaction with suitable thioalkylamines.

REFERENCES:
patent: 4290947 (1981-09-01), Christensen
patent: 4292436 (1981-09-01), Liu
patent: 4329481 (1982-05-01), Liu
patent: 4378315 (1983-03-01), Christensen
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patent: 4552696 (1985-11-01), Kim
patent: 4640799 (1987-02-01), Kim
March, Advanced Organic Chemistry, pp. 296-297, (1985).
Flockerzi, Helv Chim Acta, 66, 2069, (1983) Abstract only.
M. Sletzinger et al., "A Facile Transformation of Bicyclic Keto Esters to Bisprotected (.+-.)-8-Epithienamycin via Enol Activation", Tetrahedron Lett., 21, 4221-4224, (1980).
D. G. Melillo et al., "A Practical Synthesis of (.+-.)-Thienamycin", Tetrahedron Lett., 21, 2783-2786, (1980).
I. Shinkai et al., "A Direct Transformation of Bicyclic Keto Esters to N-Formimidoyl Thienamycin", Tetrahedron Lett., 23, 4903-4906, (1982).

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