Trifluoroacetic acid → HCID 67439980, compound

HRID 1801396Notes

Reaction equation

HRID 1801396 reaction equation
O[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=2)[NH:5][CH:4]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]([CH3:29])([CH3:28])[C:24]([O:26][CH3:27])=[O:25])[CH:17]=2)[C:3]1([CH3:31])[CH3:30].C([SiH](CC)CC)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH3:27][O:26][C:24](=[O:25])[C:23]([CH3:29])([O:22][C:18]1[CH:17]=[C:16]([CH:4]2[C:3]([CH3:31])([CH3:30])[CH2:2][C:11]3[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=3)[NH:5]2)[CH:21]=[CH:20][CH:19]=1)[CH3:28]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 12052TriethylsilaneHCID 67442141HCID 67442141, compound

Product 1

HCID 67439980HCID 67439980, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of methyl 4-hydroxy-2-(3-(1-methoxy-2-methyl-1-oxopropan-2-yloxy)phenyl)-3,3-dim ethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (510 mg, 1.19 mmol) and triethylsilane (400 mg, 3.44 mmol) in dichloromethane (6 mL) was stirred and cooled with a ice bath. A solution of trifluoroacetic acid (554 mg, 4.86 mmol) in dichloromethane (6 mL) was added slowly to the mixture. The reaction mixture was treated with sodium carbonate, and stirred for 30 min. The mixture was filtered, and the filtrate was concentrated and purified by column chromatography (silica gel, petroleum ether: ethyl acetate=15:1) to afford 230 mg of methyl 2-(3-(1-methoxy-2-methyl-1-oxopropan-2-yloxy)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate. (Yield: 47%).

Workup

  1. temperaturecooled with a ice bath
  2. stirringstirred for 30 min
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. custompurified by column chromatography (silica gel, petroleum ether: ethyl acetate=15:1)

Sources & evidence

ORD record
ord-4ede266e983d43f8941c70560e44ad48
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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