Trifluoroacetic acid → HCID 68448200, compound

HRID 450829Notes

Reaction equation

HRID 450829 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH:18]([C:19]([NH:21][CH2:22][CH2:23][C:24]2[CH:25]=[C:26]([CH2:30][C:31]([O:33]CC3C=CC(OC)=CC=3)=[O:32])[CH:27]=[CH:28][CH:29]=2)=[O:20])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](=[O:43])[N:10]1[CH:44]1[CH2:49][CH2:48][CH2:47][CH2:46][CH:45]1[OH:50].FC(F)(F)C(O)=O>C(Cl)CCl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH:18]([C:19]([NH:21][CH2:22][CH2:23][C:24]2[CH:25]=[C:26]([CH2:30][C:31]([OH:33])=[O:32])[CH:27]=[CH:28][CH:29]=2)=[O:20])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](=[O:43])[N:10]1[CH:44]1[CH2:49][CH2:48][CH2:47][CH2:46][CH:45]1[OH:50]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 72303229HCID 72303229, compound

Product 1

HCID 68448200HCID 68448200, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a mixture of 990 mg of 4-methoxybenzyl (3-{2-[({(3RS,4RS)-3-(2,4-dichlorophenyl)-2-[(1SR,2SR)-2-hydroxycyclohexyl]-1-oxo-1,2,3,4-tetrahydroisoquinolin-4-yl}carbonyl)amino]ethyl}phenyl)acetate and 10 ml of ethylene chloride was added 10 ml of trifluoroacetic acid at room temperature, followed by stirring for 4 hours. The reaction solution was concentrated under reduced pressure. The residue was dissolved in 20 mL of methanol, and 20 mL of a saturated aqueous sodium hydrogen carbonate solution was added thereto at room temperature, followed by stirring for 30 minutes. The organic solvent was evaporated under reduced pressure, and the residue was diluted with ethyl acetate and neutralized with 1 M hydrochloric acid. The product was extracted with ethyl acetate, and the organic layer was washed with a saturated aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (eluent: chloroform-methanol) to obtain 339 mg of (3-{2-[({(3RS,4RS)-3-(2,4-dichlorophenyl)-2-[(1SR,2SR)-2-hydroxycyclohexyl]-1-oxo-1,2,3,4-tetrahydroisoquinolin-4-yl}carbonyl)amino]ethyl}phenyl)acetic acid as a colorless solid.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in 20 mL of methanol
  3. addition20 mL of a saturated aqueous sodium hydrogen carbonate solution was added
  4. customat room temperature
  5. stirringby stirring for 30 minutes
  6. customThe organic solvent was evaporated under reduced pressure
  7. additionthe residue was diluted with ethyl acetate and neutralized with 1 M hydrochloric acid
  8. extractionThe product was extracted with ethyl acetate
  9. washthe organic layer was washed with a saturated aqueous sodium chloride solution
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationThe organic layer was concentrated under reduced pressure
  12. customthe obtained residue was purified by silica gel column chromatography (eluent: chloroform-methanol)

Sources & evidence

ORD record
ord-722816fbbf3d40e79f1281d2476e8128
Source dataset
uspto-grants-2013_07
Patent number
US08486970B2

Reaction notes

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