Sodium Hydroxide → HCID 66633557, compound

HRID 931824Notes

Reaction equation

HRID 931824 reaction equation
C([O:7][CH2:8][C@@H:9]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[C:10]1[C:11]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]=[C:15]([N:21]1[CH:25]=[CH:24][N:23]=[CH:22]1)[CH:14]=[CH:13]2)(=O)C(C)(C)C.[OH-].[Na+]>O1CCCC1.CO.O>[C:34]([O:33][C@@H:9]([C:10]1[C:11]([C:26]2[CH:27]=[CH:28][C:29]([Cl:32])=[CH:30][CH:31]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]=[C:15]([N:21]1[CH:25]=[CH:24][N:23]=[CH:22]1)[CH:14]=[CH:13]2)[CH2:8][OH:7])([CH3:37])([CH3:35])[CH3:36]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 66633620HCID 66633620, compound

Product 1

HCID 66633557HCID 66633557, compoundYield 98.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2-(1H-imidazol-1-yl)-7-methylquinolin-6-yl)ethyl pivalate (39.2 mg, 0.075 mmol) in tetrahydrofuran and methanol (5:1, 1 mL) was added 1 M sodium hydroxide (2 mL) and the reaction was heated to 45° C. overnight. The reaction was cooled to room temperature, diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated. The crude extract was co-evaporated two times with acetonitrile to give a clear white oil (32.1 mg). LCMS-ER+ (m/z): [M+H]+ calcd for C25H27ClN3O2: 436.17. found: 436.86.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. extractionThe crude extract

Sources & evidence

ORD record
ord-91520dce695b41d194c3da2fda86ab68
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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