(Diethylamino)sulfur trifluoride → tert-Butyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(tetrahydrofuran-3-yl)acrylate

HRID 56777

반응식

HRID 56777 반응식
C(N(S(F)(F)F)CC)C.[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([C:41]#[N:42])=[C:15]([C:17]2[C:22]([O:23][CH3:24])=[CH:21][N:20]([CH:25]([CH:33](O)[CH:34]3[CH2:38][CH2:37][O:36][CH2:35]3)[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:19](=[O:40])[CH:18]=2)[CH:16]=1.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([C:41]#[N:42])=[C:15]([C:17]2[C:22]([O:23][CH3:24])=[CH:21][N:20]([C:25](=[CH:33][CH:34]3[CH2:38][CH2:37][O:36][CH2:35]3)[C:26]([O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:27])[C:19](=[O:40])[CH:18]=2)[CH:16]=1

참가 물질

5

실험 절차

At RT, 0.5 ml (3.8 mmol, 1.2 eq.) of diethylaminosulphur trifluoride was added dropwise to a solution of 1.55 mg (3.13 mmol) of tert-butyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-hydroxy-3-(tetrahydrofuran-3-yl)propanoate (diastereomer mixture) in 48 ml of dichloromethane, the mixture was stirred at RT for 90 min and 50 ml of dichloromethane and 50 ml of saturated aqueous sodium bicarbonate solution were then added. After phase separation, the aqueous phase was extracted with dichloromethane. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried (sodium sulphate), filtered, concentrated under reduced pressure and dried. Yield: 1.38 g (93% of theory)

후처리

  1. customAfter phase separation
  2. extractionthe aqueous phase was extracted with dichloromethane
  3. washThe combined organic phases were washed with saturated aqueous sodium chloride solution
  4. dry with materialdried (sodium sulphate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customdried

출처 및 근거

ORD 기록
ord-52fe372853a54386b7cb428a3a08a36e
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434690B2

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