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US 7,396,930 B2Granted
Process for producing cyclic thioether and synthetic intermediate thereof
AssigneeSankyo Company, Limited
InventorsHiroshi Tomori, Keijiro Kobayashi, Fumihiko Toriyama
Life of this patent
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Abstract
A process for producing cyclic thioether compounds and their synthetic intermediates. The process produces a compound represented by formula (5): wherein G1 is an alkylene group, R1 is a thiol protecting group, R2 is hydrogen or an amino protecting group, and Ar is an aryl group or a 5- to 7-membered heteroaryl group.
Claims11
A process for producing a compound having the following formula (6):
- wherein R2 represents a hydrogen atom or an amino protecting group, G1 represents a C1-C6 alkylene group and Ar represents an unsubstituted phenyl group or a phenyl group substituted with at least one group from Substituent group α;
- Substituent group α is selected from the group consisting of a C1-C6 alkyl group, a C1-C6 alkoxy group and a C1-C6 alkylthio group,
- comprising reacting a compound having the formula (1):
- wherein X1 and X2 are the same or different and each represents a halogen atom, and G1 and Ar have the same meanings as defined above, with a compound having the formula (2):
- wherein R1 represents a thiol protecting group, to produce a compound represented by the formula (3):
- wherein R1, G1, X2 and Ar have the same meanings as defined above, and
- after reacting the compound of formula (3) with a metal or organometallic reagent that forms a carbanion of the compound of formula (3),
- reacting a compound having the formula (4):
- wherein R2 has the same meaning as defined above, with the resulting reaction mixture to produce a compound having the formula (5):
- wherein R1, R2, G1 and Ar have the same meanings as defined above, carrying out a dehydration reaction after removal of the group R1 of the compound having the formula (5), and
- optionally protecting the nitrogen atom with an amino protecting group.
8 more elements
A process for producing a compound having the formula (6):
- wherein R2 represents a hydrogen atom or an amino protecting group, G1 represents a C1-C6 alkylene group, and Ar represents an unsubstituted phenyl group or a phenyl group substituted with at least one group from Substituent group α;
- Substituent group α is selected from the group consisting of a C1-C6 alkyl group, a C1-C6 alkoxy group and a C1-C6 alkylthio group,
- comprising carrying out a dehydration reaction after removing a group R1 from a compound represented by formula (5):
- wherein R1 represents a thiol protecting group, and R2, G1 and Ar have the same meanings as defined above, and
- then optionally protecting the nitrogen atom with an amino protecting group.
2 more elements
Dependencies are inferred from the claim text.