Methanesulfonic Acid → Ethyl 2-oxo-1-azacyclodecane-10-carboxylate

HRID 5390

反応式

HRID 5390 の反応式
[CH2:1]([O:3][C:4]([CH:6]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[O:15])=[O:5])[CH3:2].CS(O)(=O)=O.[N-:21]=[N+]=[N-].[Na+].[OH-].[NH4+]>C(Cl)(Cl)Cl>[O:15]=[C:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[NH:21]1

参加物

6

反応物 4

HCID 6395Methanesulfonic AcidHCID 14923Ammonium HydroxideHCID 33557Sodium AzideHCID 107210Ethyl 2-oxocyclononanecarboxylate

生成物 1

HCID 19930826Ethyl 2-oxo-1-azacyclodecane-10-carboxylate

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
0 °C

実験手順

2-Ethoxycarbonyl-cyclononanone (13.72 g, 64.7 mmol) is dissolved in chloroform (200 mL) and cooled to 0° C. Methanesulfonic acid (62.4 g, 650 mmol) is added, followed by sodium azide (12.68 g, 195 mmol). The reaction is stirred at room temperature for 30 minutes, and then heated to reflux for 4 hours. The reaction mixture is poured onto ice, made basic with concentrated ammonium hydroxide (pH=9), and extracted several times with methylene chloride. The combined organic layers are dried (MgSO4), and the solvent is evaporated. The product is purified by silica gel chromatography (40% ethyl acetate/hexane) to give ethyl 2-oxo-1-azacyclodecane-10-carboxylate, m.p. 101°-103° C.

後処理

  1. temperatureheated
  2. temperatureto reflux for 4 hours
  3. additionThe reaction mixture is poured onto ice
  4. extractionextracted several times with methylene chloride
  5. dry with materialThe combined organic layers are dried (MgSO4)
  6. customthe solvent is evaporated
  7. customThe product is purified by silica gel chromatography (40% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-457a83af2b8e486aa8de7028583f3486
出典データセット
uspto-grants-1993_09
特許番号
US05244889

関連ノート

読み込み中…