Isobutyryl chloride → Tert-butyl (2-isobutyramido-4-(thiophen-2-yl)phenyl)carbamate

HRID 62670

反応式

HRID 62670 の反応式
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[CH:5]=[CH:4][C:3]=1[NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17].[C:21](Cl)(=[O:25])[CH:22]([CH3:24])[CH3:23]>ClCCl.O>[C:21]([NH:1][C:2]1[CH:7]=[C:6]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[CH:5]=[CH:4][C:3]=1[NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:19])[CH3:18])(=[O:25])[CH:22]([CH3:24])[CH3:23]

参加物

5

反応物 2

HCID 62325Isobutyryl chlorideHCID 57717474tert-Butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamate

生成物 1

HCID 71007313Tert-butyl (2-isobutyramido-4-(thiophen-2-yl)phenyl)carbamate収率 81%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of tert-butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamate (200 mg, 0.689 mmol) in dichloromethane (4 mL) was added isobutyryl chloride (0.08 mL, 0.76 mmol, 1 equiv.) and TEA (0.23 mL, 1.72 mmol, 2.5 equiv.) at 0° C. The reaction was warmed to room temperature and stirred for 16 h. The reaction was then diluted with dichloromethane and water. The organic layers were washed with water and brine, dried over Na2SO4 and concentrated. The crude material was purified by column chromatography (silica gel, EtOAc/hexanes) to afford tert-butyl (2-isobutyramido-4-(thiophen-2-yl)phenyl)carbamate (0.2 g, 81% yield).

後処理

  1. washThe organic layers were washed with water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe crude material was purified by column chromatography (silica gel, EtOAc/hexanes)

出典と根拠

ORDレコード
ord-0b625983cee54cefb2c94de1ba51cf0f
出典データセット
uspto-grants-2016_09
特許番号
US09447030B2

関連ノート

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