Sodium Hydroxide → (S)-6-(1-tert-butoxy-2-hydroxyethyl)-5-(4-chlorophenyl)-7-methylquinolin-2(1H)-one

HRID 931750Notes

Reaction equation

HRID 931750 reaction equation
C([O:7][CH2:8][C@@H:9]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:10]1[C:11]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[NH:16][C:15](=[O:21])[CH:14]=[CH:13]2)(=O)C(C)(C)C.[OH-].[Na+]>C1COCC1.CO.O>[C:30]([O:29][C@@H:9]([C:10]1[C:11]([C:22]2[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[NH:16][C:15](=[O:21])[CH:14]=[CH:13]2)[CH2:8][OH:7])([CH3:33])([CH3:31])[CH3:32]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 66631890HCID 66631890, compound

Product 1

HCID 66633284(S)-6-(1-tert-butoxy-2-hydroxyethyl)-5-(4-chlorophenyl)-7-methylquinolin-2(1H)-oneYield 92.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To the solution of (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-oxo-1,2-dihydroquinolin-6-yl)ethyl pivalate (5.8 mg) in THF and methanol (1.5 mL/0.5 mL) was added 1 M NaOH solution (0.6 mL). The mixture was stirred at 25° C. for 16 hours, diluted with water. The mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. Concentration gave (S)-6-(1-tert-butoxy-2-hydroxyethyl)-5-(4-chlorophenyl)-7-methylquinolin-2(1H)-one (4.4 mg). LCMS-ESI+ (m/z): 386.2 (M+H)+.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationConcentration

Sources & evidence

ORD record
ord-5f34137ea2b14af1869379d7341361ce
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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