Beta-lactams and their production
AssigneeSumitomo Pharmaceuticals Company, Limited
InventorsMakoto Sunagawa, Akira Sasaki, Koshiro Goda
Life of this patent
Estimating the term…
Abstract
A beta-lactam compound of the formula: ##STR1## wherein R.sub.1 and R.sub.2 are, the same or different, each a hydrogen atom or a lower alkyl group, R.sub.3.sup.0 is a hydroen atom or a lower alkyl group having a beta-configuration, R.sub.4 is a carboxyl-protecting group, X is a hydrogen atom or a protected hydroxyl group and COZ is a protected thiolcarboxyl group, which is useful as a valuable intermediate in the stereospecific production of 1-alkylcarbapenem compounds.
Claims20
A process for preparing carbapenem compounds of the formula:
- ##STR57## wherein R.sub.1 and R.sub.2 are, the same or different, each a hydrogen atom or a lower alkyl group, R.sub.3.sup.0 is a lower alkyl group having a beta-configuration, R.sub.4 is a carboxyl-protecting group, X is a hydrogen atom or a protected hydroxyl group and L is an activated hydroxyl group, which comprises subjecting a compound of the formula:
- ##STR58## wherein R.sub.1, R.sub.2, R.sub.3.sup.0, R.sub.4 and X are each as defined above and COZ is a protected thiolcarboxyl group to (a) treatment with a base, (b) treatment with an alkylating or acylating agent for catching of the residue Z.sup.- and (c) treatment with a hydroxyl-activating agent in order, said treatments (a), (b) and (c) being carried out without isolation of the intermediates as produced.
A process for preparing carbapenem compounds of the formula:
- ##STR59## wherein R is an organic group, R.sub.1 and R.sub.2 are, the same or different, each a lower alkyl group, R.sub.3.sup.0 is a hydrogen atom or a lower alkyl group having a beta-configuration, R.sub.4 is a carboxyl-protecting group and X is a hydrogen atom or a protected hydroxyl group, which comprises subjecting a compound of the formula:
- ##STR60## wherein R.sub.1, R.sub.2, R.sub.3.sup.0, R.sub.4 and X are each as defined above and COZ is a protected thiolcarboxyl group to (a) treatment with a base, (b) treatment with an alkylating or acylating agent for catching of the residue Z.sup.- and (c) treatment with a hydroxyl-activating agent in order, followed by (d) reacting the resulting product of the formula:
- ##STR61## wherein R.sub.1, R.sub.2, R.sub.3.sup.0, R.sub.4 and X are each as defined above and L is an activated hydroxyl group with a compound of the formula:
- HSR (X)
- wherein R is as defined above in the presence of a base or with a salt of the compound (X) with the base, said treatments (a), (b) and (c) or (a), (b), (c) and (d) being carried out without isolation of the intermediates as produced.
Dependencies are inferred from the claim text.