Trifluoroacetic acid → HCID 58452568, compound

HRID 70536Notes

Reaction equation

HRID 70536 reaction equation
FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1.[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([C:25]#[C:26][C@@H:27]2[N:31](CC3C=CC(OC)=CC=3OC)[C:30](=[O:43])[CH2:29][CH2:28]2)=[N:21][C:22]=1[O:23][CH3:24]>>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([C:25]#[C:26][C@@H:27]2[NH:31][C:30](=[O:43])[CH2:29][CH2:28]2)=[N:21][C:22]=1[O:23][CH3:24]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 58452822(5R)-5-[(5-Chloro-6-methoxypyridin-2-yl)ethynyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one

Product 1

HCID 58452568HCID 58452568, compoundYield 82%

Conditions

Temperature
80 °C

Procedure

Trifluoroacetic acid (4 mL) and anisole (2 mL) were added to (5R)-5-[(5-chloro-6-methoxypyridin-2-yl)ethynyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one (457 mg), and the mixture was stirred at 80° C. for two hours. The reaction solution was concentrated, and the residue was diluted with chloroform, washed with saturated aqueous sodium bicarbonate and brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→0:1) to give the title compound as a colorless oil (234 mg, 82%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionthe residue was diluted with chloroform
  3. washwashed with saturated aqueous sodium bicarbonate and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→0:1)

Sources & evidence

ORD record
ord-f892af96d00c421e9e067aca38e9ec4c
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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