Ethyl chloroformate → Tert-butyl ethyl (4-(thiophen-2-yl)-1,2-phenylene)dicarbamate

HRID 2201685

反応式

HRID 2201685 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].Cl[C:22]([O:24][CH2:25][CH3:26])=[O:23]>ClCCl.CN(C1C=CN=CC=1)C.O>[S:9]1[CH:10]=[CH:11][CH:12]=[C:8]1[C:6]1[CH:5]=[CH:4][C:3]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[C:2]([NH:1][C:22](=[O:23])[O:24][CH2:25][CH3:26])[CH:7]=1

参加物

6

反応物 2

HCID 10928Ethyl chloroformateHCID 57717474tert-Butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamate

生成物 1

HCID 71007309Tert-butyl ethyl (4-(thiophen-2-yl)-1,2-phenylene)dicarbamate収率 44%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒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 (0.20 g, 0.69 mmol, 1.0 equiv.) in dichloromethane (4 mL) was added ethyl chloroformate (0.08 mL, 0.83 mmol, 1.2 equiv.), TEA (0.19 mL, 1.37 mmol, 2.0 equiv.) and DMAP (8 mg, 0.07 mmol, 0.1 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 layer was separated, washed with water and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude material was purified on column chromatography (silica gel, 20% EtOAc/hexanes) to give tert-butyl ethyl (4-(thiophen-2-yl)-1,2-phenylene)dicarbamate (0.11 g, 44% yield).

後処理

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified on column chromatography (silica gel, 20% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-db55e1f2f4cb4fb69d87d452b8104580
出典データセット
uspto-grants-2016_06
特許番号
US09365498B2

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