2-Quinolinecarboxylic acid,1-[2-(benzoylthio)-1-oxopropyl]-1,2,3,4-tetrahydro- → (+/-)-1,2,3,4-Tetrahydro-1-(3-mercapto-1-oxopropyl)-6-methoxy-2-quinolinecarboxylic acid
Reaction equation
C([S:9][CH2:10][CH2:11][C:12]([N:14]1[C:23]2[C:18](=[CH:19][C:20]([O:24][CH3:25])=[CH:21][CH:22]=2)[CH2:17][CH2:16][CH:15]1[C:26]([OH:28])=[O:27])=[O:13])(=O)C1C=CC=CC=1.C(SC(C)C(N1C2C(=CC=CC=2)CCC1C(O)=O)=O)(=O)C1C=CC=CC=1>>[SH:9][CH2:10][CH2:11][C:12]([N:14]1[C:23]2[C:18](=[CH:19][C:20]([O:24][CH3:25])=[CH:21][CH:22]=2)[CH2:17][CH2:16][CH:15]1[C:26]([OH:28])=[O:27])=[O:13]Participants
3
Reactant 2
Product 1
Procedure
By substituting (±) 1-(3-benzoylthio-1-oxopropyl)-1,2,3,4-tetrahydro-6-methoxy-2-quinolinecarboxylic acid for the (±) 1-(2-benzoylthio-1-oxopropyl)-1,2,3,4-tetrahydro-2-quinolinecarboxylic acid in the procedure of Example 21, (±)-1,2,3,4-tetrahydro-1-(3-mercapto-1-oxopropyl)-6-methoxy-2-quinolinecarboxylic acid was obtained as an oily residue. The dicyclohexylamine salt was prepared by the addition of dicyclohexylamine to a solution of the free acid in ether. The (±)-1,2,3,4-tetrahydro-1-(3-mercapto-1-oxopropyl)-6-methoxy-2-quinolinecarboxylic acid dicyclohexylamine salt thus obtained was recrystallized from acetonitrile; yield 0.9 g, m.p. 195°-197°.
Sources & evidence
- ORD record
- ord-6f0de99cf5d14122904eb3b80234d42b
- Source dataset
- uspto-grants-1984_07
- Patent number
- US04461896
Reaction notes
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