Sodium Iodide → (2S, 4S)-2-Carbamoyl-4-(4-methoxybenzylthio)-1-(2-fluoroethyl)pyrrolidine

HRID 5070

反応式

HRID 5070 の反応式
Br[CH2:2][CH2:3][F:4].[I-].[Na+].C(=O)(O)[O-].[Na+].[C:12]([C@@H:15]1[CH2:19][C@H:18]([S:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[CH2:17][NH:16]1)(=[O:14])[NH2:13]>CN(C)C=O>[C:12]([C@@H:15]1[CH2:19][C@H:18]([S:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=2)[CH2:17][N:16]1[CH2:2][CH2:3][F:4])(=[O:14])[NH2:13]

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 129822-Fluoroethyl bromideHCID 516892Sodium Bicarbonate2 回HCID 14880267(2S, 4S)-2-Carbamoyl-4-(4-methoxybenzylthio)-pyrrolidine

生成物 1

HCID 10781417(2S, 4S)-2-Carbamoyl-4-(4-methoxybenzylthio)-1-(2-fluoroethyl)pyrrolidine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

0.4 ml of 1-bromo-2-fluoroethane, 3.83 g of sodium iodide and 0.38 g of sodium bicarbonate were added to a solution of 1.2 g of (2S, 4S)-2-carbamoyl-4-(4-methoxybenzylthio)pyrrolidine dissolved in 12 ml of dry dimethylformamide, whilst ice-cooling, and the mixture was stirred at room temperature for 20 minutes and then at 40° C. for 20 hours. At the end of this time, the reaction mixture was poured into a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, and the residue was subjected to column chromatography through silica gel (Katayama Chemicals Industries Co., silica gel 60K070). 838 mg of the title compound, melting of 122°-123° C., were obtained as a powder from those fractions eluted with ethyl acetate.

後処理

  1. temperaturecooling
  2. waitat 40° C. for 20 hours
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was then removed by distillation under reduced pressure
  7. custommelting of 122°-123° C.
  8. customwere obtained as a powder from those fractions
  9. washeluted with ethyl acetate

出典と根拠

ORDレコード
ord-968f75398c654623b4623e870b77110f
出典データセット
uspto-grants-1993_09
特許番号
US05242914

関連ノート

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