Trifluoroacetic acid → HCID 52914644, compound

HRID 2177677Notes

Reaction equation

HRID 2177677 reaction equation
[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19]C(C)(C)C)=[O:18])=[C:15]([O:24][CH2:25][C:26]#[N:27])[C:14]([C:28]3[CH:32]=[CH:31][O:30][CH:29]=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O>C(Cl)Cl.O>[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([OH:19])=[O:18])=[C:15]([O:24][CH2:25][C:26]#[N:27])[C:14]([C:28]3[CH:32]=[CH:31][O:30][CH:29]=3)=[CH:13][CH:12]=2)(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67107895HCID 67107895, compound2×

Product 1

HCID 52914644HCID 52914644, compoundYield 63.7%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6344DichloromethaneSolvent

Procedure

t-Butyl 6-(benzenesulphonylmethyl)-2-(cyanomethoxy)-3-(furan-3-yl)benzoate (Intermediate 119, 0.043 g) was dissolved in DCM (2 ml) and water (1 drop) was added followed by trifluoroacetic acid (1 ml). The mixture was stirred at room temperature for 15 minutes then it was evaporated to dryness. The residue was redissolved in DCM and re-evaporated twice. The residue was purified by preparative HPLC (C18) eluting with a mixture of acetonitrile and water containing 0.1% formic acid with a gradient of 40-55%. After evaporation, the residue was triturated with ether and the solid was collected by filtration to give 6-(benzenesulphonylmethyl)-2-(cyanomethoxy)-3-(furan-3-yl)benzoic acid (0.024 g) as a white solid.

Workup

  1. customit was evaporated to dryness
  2. dissolutionThe residue was redissolved in DCM
  3. customre-evaporated twice
  4. customThe residue was purified by preparative HPLC (C18)
  5. washeluting with a mixture of acetonitrile and water containing 0.1% formic acid with a gradient of 40-55%
  6. customAfter evaporation
  7. customthe residue was triturated with ether
  8. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-f42011e084c245e1b84952388fafa11e
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

Loading…