Perchloric Acid → (S)-2-tert-butoxy-2-(7-chloro-5-(4-chlorophenyl)-2-methylquinolin-6-yl)ethyl pivalate

HRID 931703Notes

Reaction equation

HRID 931703 reaction equation
[C:1]([O:7][CH2:8][C@H:9]([C:11]1[C:12]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)=[C:13]2[C:18](=[CH:19][C:20]=1[Cl:21])[N:17]=[C:16]([CH3:22])[CH:15]=[CH:14]2)[OH:10])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].Cl(O)(=O)(=O)=O>C(OC(=O)C)(C)(C)C>[C:1]([O:7][CH2:8][C@@H:9]([O:10][C:2]([CH3:4])([CH3:3])[CH3:1])[C:11]1[C:12]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)=[C:13]2[C:18](=[CH:19][C:20]=1[Cl:21])[N:17]=[C:16]([CH3:22])[CH:15]=[CH:14]2)(=[O:6])[C:2]([CH3:4])([CH3:5])[CH3:3]

Participants

4

Reactant 2

HCID 24247Perchloric AcidHCID 86691973(S)-2-(7-chloro-5-(4-chlorophenyl)-2-methylquinolin-6-yl)-2-hydroxyethyl pivalate

Product 1

HCID 66631574(S)-2-tert-butoxy-2-(7-chloro-5-(4-chlorophenyl)-2-methylquinolin-6-yl)ethyl pivalateYield 155.3%

Reagents, catalysts & solvents 1

HCID 10908tert-Butyl acetateSolvent

Procedure

To a stirred solution of (S)-2-(7-chloro-5-(4-chlorophenyl)-2-methylquinolin-6-yl)-2-hydroxyethyl pivalate (H) (25 mg, 0.058 mmol) in t-butylacetate (3 mL) was added 70% perchloric acid (0.02 mL, 0.23 mmol) at 0° C. The mixture was stirred at room temperature for 2 hours and quenched by the slow addition of a NaHCO3 solution. 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 1J (22 mg, 78%). LCMS-ESI+ (m/z): 488.2, 490.2 (M+H)+.

Workup

  1. customquenched by the slow addition of a NaHCO3 solution
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe obtained residue was purified by flash chromatography

Sources & evidence

ORD record
ord-3719e1a120094f039cb6ef62a6fd02be
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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