Trifluoromethanesulfonic acid, lithium salt → HCID 58997641, compound

HRID 1592368Notes

Reaction equation

HRID 1592368 reaction equation
[O:1]1[CH2:3][C@H:2]1[C@H:4]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH3:5].[F:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][NH2:24])=[CH:17][CH:16]=1.FC(F)(F)S([O-])(=O)=O.[Li+]>C(#N)C>[C:9]([O:8][C:7](=[O:13])[NH:6][C@H:4]([CH3:5])[C@@H:2]([OH:1])[CH2:3][NH:24][CH2:23][CH2:22][CH2:21][C:18]1[CH:17]=[CH:16][C:15]([F:14])=[CH:20][CH:19]=1)([CH3:12])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 3664839Trifluoromethanesulfonic acid, lithium saltHCID 64837963-(4-Fluorophenyl)propan-1-amineHCID 58997630HCID 58997630, compound

Product 1

HCID 58997641HCID 58997641, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The product from step c (823 mg, 4.39 mMol) and 3-(4-fluorophenyl)propylamine (674 mg, 4.39 mMol) were dissolved in anhydrous acetonitrile (10 ml). To this solution, lithium trifluoromethanesulfonate (1.44 g, 9.23 mMol) was added, and the solution was stirred overnight. The mixture was concentrated in-vacuo, then the residue was dissolved in EtOAc (60 ml), washed with saturated sodium bicarbonate (2×20 ml), followed by water (20 ml). The organic phase was dried over sodium sulfate and concentrated to a yellow oil. Purified via flash chromatography, eluting with EtOAc, 2.5% 7N NH4 in MeOH/EtOAc, 5% 7N NH4 in MeOH/EtOAc to yield 1.2 g of a colorless oil as product. ESI+MS detects 341 (M+H).

Workup

  1. concentrationThe mixture was concentrated in-vacuo
  2. dissolutionthe residue was dissolved in EtOAc (60 ml)
  3. washwashed with saturated sodium bicarbonate (2×20 ml)
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated to a yellow oil
  6. customPurified via flash chromatography
  7. washeluting with EtOAc, 2.5% 7N NH4 in MeOH/EtOAc, 5% 7N NH4 in MeOH/EtOAc

Sources & evidence

ORD record
ord-175436b362ad41f293b9822036346d20
Source dataset
uspto-grants-2007_11
Patent number
US07291744B2

Reaction notes

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