Sodium Hydroxide → HCID 66630502, compound

HRID 931822Notes

Reaction equation

HRID 931822 reaction equation
C([O:7][CH2:8][C@@H:9]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[C:10]1[C:11]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]=[C:15]([CH:21]([CH3:23])[CH3:22])[CH:14]=[CH:13]2)(=O)C(C)(C)C.[OH-].[Na+]>O1CCCC1.CO.O>[C:32]([O:31][C@@H:9]([C:10]1[C:11]([C:24]2[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]=[C:15]([CH:21]([CH3:22])[CH3:23])[CH:14]=[CH:13]2)[CH2:8][OH:7])([CH3:34])([CH3:35])[CH3:33]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66631760(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2-isopropyl-7-methylquinolin-6-yl)ethyl pivalate

Product 1

HCID 66630502HCID 66630502, compoundYield 96.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2-isopropyl-7-methylquinolin-6-yl)ethyl pivalate (77 mg, 0.156 mmol) in tetrahydrofuran/methanol (2:1, 1 mL) was added 1 M sodium hydroxide (2 mL) and the reaction was heated to 45° C. overnight. The reaction mixture was cooled to room temperature and diluted with water, extracted with ethyl acetate and washed with brine. The organic layer was then dried over sodium sulfate and concentrated, followed by co-evaporation with acetonitrile to give a clear oil (62 mg). LCMS-ESI+ (m/z): [M+H]+ calcd for C25H31ClNO2: 412.20. found: 412.96.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialThe organic layer was then dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ba882e5158bf4ed7bab0d003f16ac517
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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