Sodium Hydroxide → 4-Methoxy-7-(tetrahydro-pyran-4-yl)-benzooxazol-2-ylamine

HRID 1611939ノート

反応式

HRID 1611939 の反応式
COC(=O)[NH:4][C:5]1[O:6][C:7]2[C:13]([CH:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[CH:12][CH:11]=[C:10]([O:20][CH3:21])[C:8]=2[N:9]=1.[OH-].[Na+]>O1CCOCC1.C(O)CO>[CH3:21][O:20][C:10]1[C:8]2[N:9]=[C:5]([NH2:4])[O:6][C:7]=2[C:13]([CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:12][CH:11]=1

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 23593640[4-Methoxy-7-(tetrahydro-pyran-4-yl)-benzooxazol-2-yl]-carbamic acid methyl ester

生成物 1

HCID 222522334-Methoxy-7-(tetrahydro-pyran-4-yl)-benzooxazol-2-ylamine収率 74.1%

試薬・触媒・溶媒 2

HCID 174Ethylene Glycol溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

To a stirred solution of 130 g (4.24 mmol) [4-methoxy-7-(tetrahydro-pyran-4-yl)-benzooxazol-2-yl]-carbamic acid methyl ester in 90 ml dioxane and 30 ml ethylene glycol was added 90 ml of a 5 N aq. sodium hydroxide solution, and the mixture was heated at 100° C. for 16 h. After cooling to room temperature, the mixture was poured onto water and extracted four times with ethyl acetate. The combined organic phases were dried over sodium sulphate and concentrated in vacuo. Flash chromatography (dichloromethane then 5/95 methanol/dichloromethane) afforded 0.78 g (74%) 4-methoxy-7-(tetrahydro-pyran-4-yl)-benzooxazol-2-ylamine as a brown solid. ES-MS m/e (%): 249 (M+H+, 100).

後処理

  1. temperatureAfter cooling to room temperature
  2. additionthe mixture was poured onto water
  3. extractionextracted four times with ethyl acetate
  4. dry with materialThe combined organic phases were dried over sodium sulphate
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-f82c0e72b049405cba7fa3830faa2dc1
出典データセット
uspto-grants-2006_01
特許番号
US06992083B2

反応ノート

読み込み中…