Sodium Hydroxide → HCID 66631530, compound

HRID 931819Notes

Reaction equation

HRID 931819 reaction equation
C([O:7][CH2:8][C@@H:9]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])[C:10]1[C:11]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]=[C:15]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1)[CH:14]=[CH:13]2)(=O)C(C)(C)C.[OH-].[Na+]>O1CCCC1.CO.O>[C:35]([O:34][C@@H:9]([C:10]1[C:11]([C:27]2[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]=[C:15]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1)[CH:14]=[CH:13]2)[CH2:8][OH:7])([CH3:38])([CH3:36])[CH3:37]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 66631734HCID 66631734, compound

Product 1

HCID 66631530HCID 66631530, compoundYield 89%

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)-7-methyl-2-(pyridin-2-yl)quinolin-6-yl)ethyl pivalate (45.2 mg, 0.085 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 oil (33.8 mg). LCMS-ESI+ (m/z): [M+H]+ calcd for C27H28ClN2O2: 447.18. found: 447.72.

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-1509e13498ec44e092b326593e8ea56d
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

Loading…