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

HRID 931703Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 931703
[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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 66631574(S)-2-tert-butoxy-2-(7-chloro-5-(4-chlorophenyl)-2-methylquinolin-6-yl)ethyl pivalateAusbeute 155,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 10908tert-Butyl acetateLösungsmittel

Versuchsvorschrift

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)+.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-3719e1a120094f039cb6ef62a6fd02be
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296758B2

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