Acetone → 4-[(2-Amino-5-bromopyridin-3-yl)sulfinyl]-2-methylbutan-2-ol

HRID 241070ノート

反応式

HRID 241070 の反応式
[NH2:1][C:2]1[C:7]([S:8][CH2:9][CH2:10][C:11]([CH3:14])([OH:13])[CH3:12])=[CH:6][C:5]([Br:15])=[CH:4][N:3]=1.CC(C)=[O:18].O.S([O-])(O[O-])(=O)=O.[K+].[K+]>CO>[NH2:1][C:2]1[C:7]([S:8]([CH2:9][CH2:10][C:11]([CH3:12])([OH:13])[CH3:14])=[O:18])=[CH:6][C:5]([Br:15])=[CH:4][N:3]=1

参加物

6

反応物 4

HCID 180AcetoneHCID 962WaterHCID 10313463Potassium peroxymonosulphateHCID 66820470HCID 66820470、化合物

生成物 1

HCID 668205914-[(2-Amino-5-bromopyridin-3-yl)sulfinyl]-2-methylbutan-2-ol収率 60%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

To a solution of 4-[(2-amino-5-bromopyridin-3-yl)thio]-2-methylbutan-2-ol (83 mg, 0.28 mmol) in a mixture of methanol (750 μL), acetone (750 μL) and water (450 μL) was added potassium peroxymonosulfate (131 mg, 0.21 mmol) and the reaction mixture was stirred for 90 minutes at 0° C. The reaction mixture was partitioned between water (20 mL) and ethyl acetate (50 mL). The organic layer was separated and washed with water (20 mL) and brine (20 mL), dried over sodium sulfate, filtered and concentrated. Purification by flash chromatography (35% to 80% ethyl acetate in hexane) gave 4-[(2-amino-5-bromopyridin-3-yl)sulfinyl]-2-methylbutan-2-ol (52 mg, 60%); MS (EI) for C10H15BrN2O2S: 308 (MH+).

後処理

  1. customThe reaction mixture was partitioned between water (20 mL) and ethyl acetate (50 mL)
  2. customThe organic layer was separated
  3. washwashed with water (20 mL) and brine (20 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography (35% to 80% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-562c0c0b70344e33823acd6ef6af8784
出典データセット
uspto-grants-2014_02
特許番号
US08648066B2

反応ノート

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