(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

Reaction equation

HRID 56777 reaction equation
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

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 117622815tert-Butyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-hydroxy-3-(tetrahydrofuran-3-yl)propanoate

Product 1

HCID 118877888tert-Butyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(tetrahydrofuran-3-yl)acrylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-52fe372853a54386b7cb428a3a08a36e
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Linked notes

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