Potassium Carbonate → (S)-ethyl 2-tert-butoxy-2-(5-(4-chlorophenyl)-2-(hydroxymethyl)-7-methylquinolin-6-yl)acetate

HRID 931768Notes

Reaction equation

HRID 931768 reaction equation
C([O:4][CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][C:10]([CH3:34])=[C:11]([C@H:23]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:12]=2[C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[N:7]=1)(=O)C.C([O-])([O-])=O.[K+].[K+]>CO.O>[C:30]([O:29][C@@H:23]([C:11]1[C:12]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=[C:13]2[C:8](=[CH:9][C:10]=1[CH3:34])[N:7]=[C:6]([CH2:5][OH:4])[CH:15]=[CH:14]2)[C:24]([O:26][CH2:27][CH3:28])=[O:25])([CH3:31])([CH3:32])[CH3:33]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 86691980(S)-ethyl 2-(2-(acetoxymethyl)-5-(4-chlorophenyl)-7-methylquinolin-6-yl)-2-tert-butoxyacetate

Product 1

HCID 68587089(S)-ethyl 2-tert-butoxy-2-(5-(4-chlorophenyl)-2-(hydroxymethyl)-7-methylquinolin-6-yl)acetateYield 62%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of (S)-ethyl 2-(2-(acetoxymethyl)-5-(4-chlorophenyl)-7-methylquinolin-6-yl)-2-tert-butoxyacetate (0.095 mmol) in methanol (2 mL) was added 2 M K2CO3 (0.5 mL, excess) at room temperature. The mixture was stirred at room temperature for 1 hour, 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 (26 mg, 62%). LCMS-ESI+ (m/z): 442.2, 444.2 (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-9a03ac812aa84a31ab46c22b6487726b
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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