Ethyl Acetate → Methyl 2-(5-bromo-2-phenyl-1,3-thiazol-4-yl)-2-(tert-butoxy)acetate

HRID 590971ノート

反応式

HRID 590971 の反応式
[Br:1]N1C(=O)CCC1=O.[C:9]([O:13][CH:14]([C:19]1[N:20]=[C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[S:22][CH:23]=1)[C:15]([O:17][CH3:18])=[O:16])([CH3:12])([CH3:11])[CH3:10].C(OCC)(=O)C>CN(C)C=O>[Br:1][C:23]1[S:22][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:20][C:19]=1[CH:14]([O:13][C:9]([CH3:12])([CH3:10])[CH3:11])[C:15]([O:17][CH3:18])=[O:16]

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 70818322Methyl 2-(tert-butoxy)-2-(2-phenyl-1,3-thiazol-4-yl)acetate

生成物 1

HCID 70819454Methyl 2-(5-bromo-2-phenyl-1,3-thiazol-4-yl)-2-(tert-butoxy)acetate収率 78%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

Under a nitrogen atmosphere, N-bromosuccinimide (108 mg, 0.6 mmol) was added to a solution of methyl 2-(tert-butoxy)-2-(2-phenyl-1,3-thiazol-4-yl)acetate (6b) (30 mg, 0.1 mmol) in N,N-dimethylformamide (2 mL). The reaction mixture was warmed at 70° C. for 3 hours and ethyl acetate (20 mL) was then added. The organic layer was washed with water (2×10 mL), brine (10 mL), dried over sodium sulfate, filtered, and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 80/20) to afford the desired product (6c) as a yellow oil (30 mg, 0.078 mmol, 78%).

後処理

  1. washThe organic layer was washed with water (2×10 mL), brine (10 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 80/20)

出典と根拠

ORDレコード
ord-bb6a946b4aee477187a315441bcb4b93
出典データセット
uspto-grants-2016_01
特許番号
US09238026B2

反応ノート

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