Lithium Hydroxide → HCID 67228292, compound
Reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:18]=[C:17]([N:19]3[CH2:24][CH2:23][N:22]([CH2:25][C:26]4[CH2:27][O:28][C:29]([CH3:40])([CH3:39])[CH2:30][C:31]=4[C:32]4[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=4)[CH2:21][CH2:20]3)[CH:16]=[CH:15][C:10]=2[C:11]([O:13]C)=[O:12])=[CH:4][C:3]=1[Cl:41].[OH-].[Li+]>O1CCCC1.CO.ClCCl.O>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:18]=[C:17]([N:19]3[CH2:24][CH2:23][N:22]([CH2:25][C:26]4[CH2:27][O:28][C:29]([CH3:39])([CH3:40])[CH2:30][C:31]=4[C:32]4[CH:33]=[CH:34][C:35]([Cl:38])=[CH:36][CH:37]=4)[CH2:21][CH2:20]3)[CH:16]=[CH:15][C:10]=2[C:11]([OH:13])=[O:12])=[CH:4][C:3]=1[Cl:41]Participants
7
Reactant 2
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 55 °C
Procedure
To a solution of EXAMPLE 387B (0.300 g) in tetrahydrofuran (5 mL) and methanol (1 mL) was added 1.0M lithium hydroxide (1.506 mL) and the suspension was heated to 55° C. After 3 hours, the reaction was cooled, diluted with dichloromethane (20 mL) and water (10 mL), and quenched with 1N aqueous HCl (1.5 mL). The organic layer was separated and the aqueous layer was extracted with 20 ml of dichloromethane. The combined organic extracts were washed with brine (25 mL), dried over magnesium sulfate, filtered, and concentrated to give the title compound.
Workup
- temperaturethe reaction was cooled
- customquenched with 1N aqueous HCl (1.5 mL)
- customThe organic layer was separated
- extractionthe aqueous layer was extracted with 20 ml of dichloromethane
- washThe combined organic extracts were washed with brine (25 mL)
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-9ae642137ad940e38efd0e3998ae6772
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952157B2
Reaction notes
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