Process for producing carbapenem compound for oral administration
View Patent ↗The present invention provides a process for efficiently producing a 1β-methylcarbapenem compound for oral administration. The process, which is for producing a 1β-methylcarbapenem compound represented by general formula (2), is characterized by reacting a β-lactam compound represented by general formula (1) as a starting material with a thiol compound (R 3 —SH) in the presence of a base and optionally eliminating the protective group R 1 . In the formulae (1) and (2), R 1 denotes a hydrogen atom, a trimethylsilyl group or a triethylsilyl group; R 2 denotes an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms; R 3 denotes an organic group; and R 4 denotes hydrogen, a trimethylsilyl group or a triethylsilyl group.
1. A process for producing a compound represented by formula (2):
that comprises reacting a compound represented by formula (1):
with a thiol compound represented by formula (3):
R 3 —SH (3)
in the presence of a base and optionally eliminating protective group R 1 :
where R 1 is a hydrogen atom, a trimethylsilyl group or a triethylsilyl group:
where R 2 is an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms:
wherein R 3 is a thiol residue of a thiol compound represented by formula(4):
and wherein R 4 is a hydrogen atom, a trimethyisilyl group or a triethyisilyl group.
2. A process for producing a compound represented by formula (2):
that comprises reacting a compound represented by formula (1):
with a thiol compound represented by formula (3):
R 3 —SH (3)
in the presence of a base and optionally eliminating protective group R 1 :
wherein R 1 is a hydrogen atom, a trimethylsilyl group or a triethylsilyl group:
wherein R 2 is an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms;
wherein R 3 is a thiol residue of a thiol compound represented by formula (5):
and wherein R 4 is a hydrogen atom, a trimethylsilyl group or a triethylsiyl group.
3. The process according to claim 1 or 2 , wherein R 2 is atert-butyl group.