Process for producing N-biphenylmethylthiadiazoline derivative or salt thereof and intermediate for producing the same
AssigneeWakunaga Seiyaku Kabushiki Kaisha
InventorsSatoshi Inoue, Nobuya Sakae, Masaharu Yokomoto, Kouji Nishimura, Terukage Hirata
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Abstract
Described is a process for producing an N-biphenyl-methylthiadiazoline derivative (7) in accordance with the reaction formula described below. According to the process of the present invention, it is possible to produce a compound (7) advantageously from the industrial viewpoint. ##STR1##
Claims10
An N-benzylthiadiazoline derivative represented by the following formula (3):
- ##STR4## wherein R.sup.1 represents a lower alkyl group, R.sup.2 represents a hydrogen atom or an acyl group and X.sup.1 represents a halogen atom, or an acid salt thereof, with the proviso that when R.sup.2 contains a benzene ring, R.sup.2 is lower aralkyloxycarbonyl.
A process for producing an N-benzylthiadiazoline derivative represented by the following formula (3):
- wherein R.sup.1 represents a lower alkyl group, X.sup.1 represents a halogen atom and R.sup.2 represents a hydrogen atom or an acyl group or an acid salt thereof, which comprises reacting an aminothiazole derivative represented by the following formula (1):
- wherein R.sup.1 and R.sup.2 have the same meanings as defined above with a halogenotoluene derivative represented by the following formula (2):
- ##STR5## wherein X.sub.1 has the same meaning as defined above, X.sup.2 represents a halogen atom or --SO.sub.3 R.sup.3 in which R.sup.3 represents an alkyl or aryl group in the presence or absence of a base and then optionally eliminating an acyl group.
A process for producing the compound represented by the following formula (5):
- ##STR6## wherein R.sup.1 represents a lower alkyl group, R.sup.2 represents a hydrogen atom or an acyl group and A represents a hydrogen atom or a tetrazolyl protective group, which comprises reacting an N-benzylthiadiazoline derivative represented by the following formula (3):
- wherein R.sup.1 and R.sup.2 have the same meanings as defined above and X.sup.1 represents a halogen atom or an acid salt of the derivative with a compound represented by the following formula (4):
- ##STR7## wherein Z represents a hydrogen atom, a copper atom, a lithium atom, a halogenated metal or a group --B(OR.sup.4).sub.2 in which R.sup.4 represents a hydrogen atom or a lower alkyl group, and A represents a hydrogen atom or a tetrazolyl protective group.
A process for producing an N-biphenylmethyl-thiadiazoline derivative represented by the following formula (7):
- wherein R.sup.1 represents a lower alkyl group or a salt thereof, which comprises reacting an N-benzylthiadiazoline derivative represented by the following formula (3):
- wherein R.sup.1 has the same meaning as defined above, R.sup.2 represents a hydrogen atom or an acyl group and X.sup.1 represents a halogen atom or an acid salt thereof with a compound represented by the following formula (4):
- ##STR8## wherein Z represents a hydrogen atom, a copper atom, a lithium atom, a halogenated metal or a group --B(OR.sup.4).sub.2 in which R.sup.4 represents a hydrogen atom or a lower alkyl group and A represents a hydrogen atom or a tetrazolyl protective group, eliminating an acyl group in the case where the compound so obtained has the acyl group, obtaining the compound represented by the following formula (5b):
- ##STR9## wherein R.sup.1 and A have the same meanings as defined above, reacting the compound (5b) with the compound represented by the following formula (6):
- ##STR10## and then eliminating the tetrazolyl protective group as needed.
Dependencies are inferred from the claim text.