Lithium Hydroxide → Trans-2-carboxy-5,7-dichloro-4-phenylmethylcarbonylamino-1,2,3,4-tetrahydroquinoline
Reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C@@H:4]([NH:17][C:18]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19])[C:5](=C=O)[C@H:6](OC)[NH:7]2.[OH-:27].[Li+].[O:29]1[CH2:33]CCC1>O>[C:33]([C@H:6]1[CH2:5][C@H:4]([NH:17][C:18]([CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:19])[C:3]2[C:8](=[CH:9][C:10]([Cl:12])=[CH:11][C:2]=2[Cl:1])[NH:7]1)([OH:29])=[O:27]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of trans-5,7-dichloro-2-methoxy-carbonyl-4-phenylmethylcarbonylamino-1,2,3,4-tetrahydroquinoline (3.11 g, 7.89 mmol) in a mixture of tetrahydrofuran (100 ml) and water (50 ml) was added aqueous lithium hydroxide (17.4 ml of a 0.5M solution, 8.70 mmol) and the resulting mixture was stirred at room temperture for 3 h. The organic solvent was removed in vacuo and the aqueous residue was acidified with concentrated hydrochloric acid and extracted with ethyl acetate (2×100 ml). The combined extracts were washed with saturated brine (1×100 ml), dried (MgSO4) and evaporated to give the crude product which was recrystallised from ethyl acetate/petroleum ether 60-80 to give the title compound as colourless crystals (2 crops, 2.65 g) identical in physical properties to example 34 step b.
Workup
- customThe organic solvent was removed in vacuo
- extractionextracted with ethyl acetate (2×100 ml)
- washThe combined extracts were washed with saturated brine (1×100 ml)
- dry with materialdried (MgSO4)
- customevaporated
- customto give the crude product which
- customwas recrystallised from ethyl acetate/petroleum ether 60-80
Sources & evidence
- ORD record
- ord-e988fd1a59784dc194f8c048ca209ffd
- Source dataset
- uspto-grants-1993_07
- Patent number
- US05231102
Reaction notes
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