Lithium Hydroxide → HCID 11613876, compound

HRID 1785972Notes

Reaction equation

HRID 1785972 reaction equation
[C:1]([N:4]([C:35]1[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=1)[C@H:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([C:15]([C:17]2[CH:32]=[CH:31][C:20]([O:21][CH2:22][CH2:23][C:24]([CH3:30])([CH3:29])[C:25]([O:27]C)=[O:26])=[C:19]([F:33])[CH:18]=2)=[O:16])[C@@H:7]([CH3:34])[CH2:6]1)(=[O:3])[CH3:2].[Li+].[OH-]>CO.C1COCC1>[C:1]([N:4]([C:35]1[CH:36]=[CH:37][C:38]([Cl:41])=[CH:39][CH:40]=1)[C@H:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([C:15]([C:17]2[CH:32]=[CH:31][C:20]([O:21][CH2:22][CH2:23][C:24]([CH3:30])([CH3:29])[C:25]([OH:27])=[O:26])=[C:19]([F:33])[CH:18]=2)=[O:16])[C@@H:7]([CH3:34])[CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57595479HCID 57595479, compound

Product 1

HCID 11613876HCID 11613876, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To the solution of methyl 4-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}-2-fluorophenoxy)-2,2-dimethylbutanoate (176 mg, 0.30 mmol) in MeOH/THF (1 mL/1 mL) was added excessive LiOH (1N aqueous solution). The reaction mixture was stirred at r.t. overnight. The reaction was quenched by adding 6N HCl to PH 2. The mixture was concentrated under reduced pressure to remove MeOH and THF. DCM (30 mL) was added. The reaction mixture was washed with brine (30 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by silica gel chromatography (hexanes-ethyl acetate system) to afford slightly yellow solid product (120 mg, 70%).

Workup

  1. customThe reaction was quenched
  2. additionby adding 6N HCl to PH 2
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customto remove MeOH and THF
  5. additionDCM (30 mL) was added
  6. washThe reaction mixture was washed with brine (30 mL)
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude residue was purified by silica gel chromatography (hexanes-ethyl acetate system)

Sources & evidence

ORD record
ord-cb467bc9a786406ab8d272b646b1c508
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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