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

HRID 5070

반응식

HRID 5070 반응식
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]

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 129822-Fluoroethyl bromideHCID 516892Sodium Bicarbonate2회HCID 14880267(2S, 4S)-2-Carbamoyl-4-(4-methoxybenzylthio)-pyrrolidine

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-968f75398c654623b4623e870b77110f
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05242914

연결된 노트

불러오는 중…