Dimethylformamide → Tert-butyl[2-[3-(3-nitro-2-pyridyloxy)phenyl]ethyl]carbamate

HRID 1373228ノート

反応式

HRID 1373228 の反応式
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:11]([O:15][C:16]([NH:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[C:11]([O:15][C:16](=[O:17])[NH:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:22]=1)([CH3:14])([CH3:12])[CH3:13]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 796132-Chloro-3-nitropyridineHCID 11031911tert-Butyl 3-hydroxyphenethylcarbamate

生成物 1

HCID 21073098Tert-butyl[2-[3-(3-nitro-2-pyridyloxy)phenyl]ethyl]carbamate収率 93.7%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

A mixture of 2-chloro-3-nitropyridine (4.76 g, 30 mmols), N-tert-butoxycarbonyl-3-hydroxyphenethylamine (7.11 g, 30 mmols), potassium carbonate (4.14 g, 30 mmols) and N,N-dimethylformamide (50 ml) was stirred at 100° C. for 12 hours. The reaction mixture was cooled, then poured into water, and then extracted with ethyl acetate. The extract was washed with water, and then dried with anhydrous magnesium sulfate, and the solvent was evaporated away. The residue was purified through silica gel column chromatography to give an yellow oil of tert-butyl[2-[3-(3-nitro-2-pyridyloxy)phenyl]ethyl]carbamate (10.1 g, 92.5%).

後処理

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customthe solvent was evaporated away
  6. customThe residue was purified through silica gel column chromatography

出典と根拠

ORDレコード
ord-4daedad2df604bd7979069e4cde21399
出典データセット
uspto-grants-2007_01
特許番号
US07160887B1

反応ノート

読み込み中…