Sodium Hydroxide → HCID 66631448, compound

HRID 931784Notes

Reaction equation

HRID 931784 reaction equation
OC(C(F)(F)F)=O.C([O:14][CH2:15][C@@H:16]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])[C:17]1[C:18]([C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)=[C:19]2[C:24](=[CH:25][C:26]=1[CH3:27])[N:23]=[C:22]([CH:28]=[CH2:29])[CH:21]=[CH:20]2)(=O)C(C)(C)C.[OH-].[Na+]>C1COCC1.CO.O>[C:38]([O:37][C@@H:16]([C:17]1[C:18]([C:30]2[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=2)=[C:19]2[C:24](=[CH:25][C:26]=1[CH3:27])[N:23]=[C:22]([CH:28]=[CH2:29])[CH:21]=[CH:20]2)[CH2:15][OH:14])([CH3:39])([CH3:40])[CH3:41]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 131735174(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-vinylquinolin-6-yl)ethyl pivalate TFA salt

Product 1

HCID 66631448HCID 66631448, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-vinylquinolin-6-yl)ethyl pivalate TFA salt (14 mg, 0.024 mmol) in THF and methanol (3 mL/1 mL) was added 1 M NaOH solution (0.5 mL, excess). The mixture was stirred at 0° C. for 6 hours and diluted with water. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated in vacuo. The obtained residue was used in the next reaction without purification. LCMS-ESI+ (m/z): 396.2, 398.2 (M+H)+.

Workup

  1. extractionThe resulting 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 used in the next reaction without purification

Sources & evidence

ORD record
ord-10da3783f6b645a3a0f161f979e389e1
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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