Sodium Hydroxide → (S)-2-tert-butoxy-2-(7-chloro-5-(4-chlorophenyl)-2-methylquinolin-6-yl)ethanol

HRID 931704Notes

Reaction equation

HRID 931704 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[Cl:20])[N:16]=[C:15]([CH3:21])[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[Cl:20])[N:16]=[C:15]([CH3:21])[CH:14]=[CH:13]2)[CH2:8][OH:7])([CH3:33])([CH3:31])[CH3:32]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 66631574(S)-2-tert-butoxy-2-(7-chloro-5-(4-chlorophenyl)-2-methylquinolin-6-yl)ethyl pivalate

Product 1

HCID 66631657(S)-2-tert-butoxy-2-(7-chloro-5-(4-chlorophenyl)-2-methylquinolin-6-yl)ethanolYield 61%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (S)-2-tert-butoxy-2-(7-chloro-5-(4-chlorophenyl)-2-methylquinolin-6-yl)ethyl pivalate (1J) (22 mg, 0.045 mmol) in THF and methanol (3 mL/1 mL) was added 1 M NaOH solution (1 mL, excess) at 0° C. The mixture was stirred at room temperature for 16 hours and diluted with water. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated in vacuo. The obtained residue was purified by flash chromatography to provide the desired product 1K (11 mg, 61%). LCMS-ESI+ (m/z): 404.2, 406.2 (M+H)+.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe obtained residue was purified by flash chromatography

Sources & evidence

ORD record
ord-fdcb84e5b41240b1a60f9f5453ea0dc8
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

Loading…