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

HRID 931703노트

반응식

HRID 931703 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 10908tert-Butyl acetate용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-3719e1a120094f039cb6ef62a6fd02be
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296758B2

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