Process for production of 4-oxoquinoline compound
The present invention provides a compound useful as a synthetic intermediate for an anti-HIV agent having an integrase inhibitory activity, a production method thereof, and a production method of an anti-HIV agent using the synthetic intermediate. Specifically, the present invention provides, for example, compounds represented by the formulas (6), (7-1), (7-2) and (8): wherein R is a fluorine atom or a methoxy group, R 1 is a C 1 -C 4 alkyl group, R 2 is a hydroxyl-protecting group, and X 2 is a halogen atom, a production method thereof, and a production method of an anti-HIV agent using the synthetic intermediate.
1. A method of producing a compound of the following formula (10):
or a salt thereof, comprising
reacting a compound of the following formula (8):
wherein R 1 is a C 1 -C 4 alkyl group, R 2 is a hydroxyl-protecting group and X 2 is a halogen atom,
to produce a compound of the following formula (9):
reacting said compound of the formula (9) to produce the above compound of formula (10) or a salt thereof.
2. A method of producing a compound of the following formula (10):
or a salt thereof, comprising
reacting a compound of the following formula (4-A):
wherein R 1 is a C 1 -C 4 alkyl group and X 2 is a halogen atom,
or a salt thereof
to produce a compound of the following formula (5-A):
reacting said compound of the formula (5-A) to produce a compound of the following formula (6-A):
reacting said compound of the formula (6-A) to produce a compound of the following formula (7-1):
wherein R 2 is a hydroxyl-protecting group;
reacting said compound of the formula (7-1) to produce a compound of the following formula (8):
reacting said compound of the formula (8) to produce a compound of the following formula (9):
reacting said compound of the formula (9) to produce the above compound of formula (10) or a salt thereof.
3. A method of producing a compound of the following formula (10):
or a salt thereof, comprising
reacting a compound of the following formula (4-B):
wherein R 1 is a C 1 -C 4 alkyl group and X 2 is a halogen atom,
or a salt thereof
to produce a compound of the following formula (5-B):
reacting said compound of the formula (5-B) to produce a compound of the following formula (6-B):
reacting said compound of the formula (6-B) to produce a compound of the following formula (7-2):
reacting said compound of the formula (7-2) to produce a compound of the following formula (8):
wherein R 2 is a hydroxyl-protecting group;
reacting said compound of the formula (8) to produce a compound of the following formula (9):
reacting said compound of the formula (9) to produce the above compound of formula (10) or a salt thereof.
4. A compound of the following formula (8):
wherein R 1 is a C 1 -C 4 alkyl group, R 2 is a hydroxyl-protecting group, and X 2 is a halogen atom.
5. A compound of the following formula (7-2):
wherein R 1 is a C 1 -C 4 alkyl group and X 2 is a halogen atom.