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

HRID 931703ノート

反応式

HRID 931703 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 10908tert-Butyl acetate溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-3719e1a120094f039cb6ef62a6fd02be
出典データセット
uspto-grants-2016_03
特許番号
US09296758B2

反応ノート

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