Ethyl bromoacetate → HCID 53212233、化合物

HRID 1175680ノート

反応式

HRID 1175680 の反応式
[CH2:1]([CH:3]1[O:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[NH:5][C:4]1=[O:13])[CH3:2].[H-].[Na+].Br[CH2:17][C:18]([O:20]CC)=[O:19]>CN(C=O)C.O>[CH2:1]([CH:3]1[O:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]([CH2:17][C:18]([OH:20])=[O:19])[C:4]1=[O:13])[CH3:2]

参加物

6

反応物 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 31555992-Ethyl-2H-benzo[b][1,4]oxazin-3(4H)-one

生成物 1

HCID 53212233HCID 53212233、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 2-ethyl-2H-benzo[b][1,4]oxazin-3(4H)-one (1.5 mmol, 260 mg) in DMF (2 ml) was added NaH (1.8 mmol, 43 mg) and the reaction mixture was stirred at room temperature for 1 h before the dropwise addition of ethyl bromoacetate (1.5 mmol, 250 mg). The reaction mixture was stirred at room temperature overnight, diluted with water and extracted with ethyl acetate. The organic layer was washed with 1N HCl, Sat. NaHCO3, dried over Na2SO4 and evaporated to dryness. The crude compound was dissolved in MeOH (3 ml) and 1 N NaOH (3 ml) and stirred for 2 h at room temperature. The MeOH was removed under reduced pressure and the resulting aqueous solution extracted with EtOAc. The aqueous layer was acidified to pH 2 with 1N HCl and extracted with EtOAc. The organic phase was dried over Na2SO4 and the solvent was evaporated to give the title compound. LC/MS (10% to 99%): M/Z (M+H)+ (obs)=236; tR=2.4.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with 1N HCl, Sat. NaHCO3
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness
  5. dissolutionThe crude compound was dissolved in MeOH (3 ml)
  6. stirring1 N NaOH (3 ml) and stirred for 2 h at room temperature
  7. customThe MeOH was removed under reduced pressure
  8. extractionthe resulting aqueous solution extracted with EtOAc
  9. extractionextracted with EtOAc
  10. dry with materialThe organic phase was dried over Na2SO4
  11. customthe solvent was evaporated

出典と根拠

ORDレコード
ord-bc53b4b1d4f742bab5fe96947ca60b75
出典データセット
uspto-grants-2010_11
特許番号
US07842686B2

反応ノート

読み込み中…