Potassium Phosphate, Tribasic → HCID 59756910, compound

HRID 1880588Notes

Reaction equation

HRID 1880588 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[O-]P([O-])([O-])=O.[K+].[K+].[K+].O[C:25]1[CH:33]=[C:32]2[C:28]([CH2:29][CH2:30][CH:31]2[CH2:34][C:35]2[CH:44]=[CH:43][C:38]([C:39]([O:41][CH3:42])=[O:40])=[CH:37][CH:36]=2)=[CH:27][CH:26]=1>C1(C)C=CC=CC=1>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:25]1[CH:33]=[C:32]2[C:28]([CH2:29][CH2:30][CH:31]2[CH2:34][C:35]2[CH:36]=[CH:37][C:38]([C:39]([O:41][CH3:42])=[O:40])=[CH:43][CH:44]=2)=[CH:27][CH:26]=1)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 67749Trifluoromethanesulfonic anhydrideHCID 69309263HCID 69309263, compound

Product 1

HCID 59756910HCID 59756910, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Trifluoromethanesulfonic anhydride (0.08 mL, 0.48 mmol) was dropwise to a solution of toluene (2 mL) and aqueous 30% K3PO4 (2 mL) containing the intermediate from Step D (63 mg, 0.22 mol). The solution was stirred at room temperature until no starting material remained by HPLC analysis. The solution was partitioned between ethyl acetate and water. The organic phase was washed with water and brine. The solution was then dried over MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography using a hexanes/ethyl acetate gradient to give the title compound. 1H NMR (500 MHz, CDCl3): δ 8.01 (d, J=8.2 Hz, 2H); 7.27 (d, J=8.1 Hz, 2H); 7.08 (dd, J=2.3, 8.2 Hz, 1H); 6.95 (d, J=2.1 Hz, 1H); 3.95 (s, 3H); 3.56-3.50 (m, 1H); 3.15 (dd, J=6.2, 13.5 Hz, 1H); 2.92-2.80 (m, 3H); 2.28-2.20 (m, 1H); 1.90-1.83 (m, 1H). LCMS2 2.71 min. (M+H)=415

Workup

  1. customThe solution was partitioned between ethyl acetate and water
  2. washThe organic phase was washed with water and brine
  3. dry with materialThe solution was then dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-9b32132ae21b44999fc079328e410960
Source dataset
uspto-grants-2012_11
Patent number
US08318760B2

Reaction notes

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