Tetrafluoroborate → HCID 21713176, compound

HRID 650714Notes

Reaction equation

HRID 650714 reaction equation
[CH2:1](/[C:4](=[CH:8]\[S:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18]([C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)=[O:19])=[CH:14][CH:13]=1)(=[O:11])=[O:10])/[C:5]([OH:7])=[O:6])[CH2:2][CH3:3].[H+].[B-](F)(F)(F)F.F[B-](F)(F)F>C(Cl)Cl>[N:23]1[CH:24]=[CH:25][C:20]([C:18]([C:15]2[CH:14]=[CH:13][C:12]([S:9]([CH2:8][CH:4]([CH2:1][CH2:2][CH3:3])[C:5]([OH:7])=[O:6])(=[O:11])=[O:10])=[CH:17][CH:16]=2)=[O:19])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 26255TetrafluoroborateHCID 28118Tetrafluoroboric acid2×HCID 21713169HCID 21713169, compound2×

Product 1

HCID 21713176HCID 21713176, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(E)-2-Propyl-3-[4-(pyridine-4-carbonyl)benzenesulfonyl]acrylic acid was converted into its HBF4 salt on treatment with 1 equivalent of HBF4 in DCM and evaporation to dryness. (E)-2-Propyl-3-[4-(pyridine-4-carbonyl)benzenesulfonyl]-acrylic acid hydrofluoroborate (0.22 g, 0.49 mmol) and [(R,R)-MeDuPHOS Rh (COD)]BF4 (6 mg, 0.49×10−2 mmol) were place in the pressure vessel under nitrogen, and then the bomb was degassed with hydrogen. Degassed methanol (10 ml) was added and the mixture was hydrogenated at 2070 kPa (300 psi) hydrogen for 16 hour at room temperature. The methanol was removed under reduced pressure. The product was treated with aqueous sodium bicarbonate and then citric acid was added until pH 4. The product was extracted into dichloromethane, which was dried over magnesium sulfate and then evaporated to give the title compound (0.15 g, 83% yield). E.e. was determined by chiral HPLC to be 96% e.e.

Workup

  1. customthe bomb was degassed with hydrogen
  2. additionDegassed methanol (10 ml) was added
  3. customThe methanol was removed under reduced pressure
  4. additionThe product was treated with aqueous sodium bicarbonate
  5. additioncitric acid was added until pH 4
  6. extractionThe product was extracted into dichloromethane, which
  7. dry with materialwas dried over magnesium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-0a602d28816d448795bb79826c1f7614
Source dataset
uspto-grants-2001_08
Patent number
US06274758B1

Reaction notes

Loading…