Trifluoroacetic acid → HCID 117701714, compound

HRID 1507449Notes

Reaction equation

HRID 1507449 reaction equation
[CH2:1]([O:8][C:9]1[C:18]([CH:19]([CH:21]2[CH2:23][CH2:22]2)O)=[C:17]2[C:12]([C:13](=[O:35])[C:14]([CH3:34])=[C:15]([CH:24]3[CH2:29][CH2:28][N:27]([C:30](=[O:33])[CH2:31][CH3:32])[CH2:26][CH2:25]3)[O:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([O:8][C:9]1[C:18]([CH2:19][CH:21]2[CH2:23][CH2:22]2)=[C:17]2[C:12]([C:13](=[O:35])[C:14]([CH3:34])=[C:15]([CH:24]3[CH2:29][CH2:28][N:27]([C:30](=[O:33])[CH2:31][CH3:32])[CH2:26][CH2:25]3)[O:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acid2×HCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 117701566HCID 117701566, compound

Product 1

HCID 117701714HCID 117701714, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-(benzyloxy)-8-[cyclopropyl(hydroxy)methyl]-3-methyl-2-(1-propanoylpiperidin-4-yl)-4H-chromen-4-one (100 mg, 0.21 mmol) obtained in Example 34-3 in dichloromethane (2 mL), triethylsilane (336 μL, 2.10 mmol) was added dropwise under cooling with ice. Then, trifluoroacetic acid (79 μL, 1.05 mmol) was added dropwise thereto, and the mixture was stirred for 15 minutes under cooling with ice and then at room temperature for 1 hour. Trifluoroacetic acid (79 μL, 1.05 mmol) was added dropwise to the reaction solution, and the mixture was further stirred at room temperature for 2 hours. The reaction solution was cooled with ice, and then a saturated aqueous solution of sodium bicarbonate (30 mL) was added dropwise thereto, followed by extraction with dichloromethane. The organic layer was dried over sodium sulfate. The desiccant was filtered off, and then the filtrate was concentrated under reduced pressure. The obtained residue was purified by NH silica gel column chromatography (n-hexane/ethyl acetate=98/2→0/100). The title compound (62 mg, yield: 64%) was obtained as an oil.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. waitat room temperature for 1 hour
  4. stirringthe mixture was further stirred at room temperature for 2 hours
  5. temperatureThe reaction solution was cooled with ice
  6. extractionfollowed by extraction with dichloromethane
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. filtrationThe desiccant was filtered off
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe obtained residue was purified by NH silica gel column chromatography (n-hexane/ethyl acetate=98/2→0/100)

Sources & evidence

ORD record
ord-ca7cc3e12c0a4c33807c3141030ed615
Source dataset
uspto-grants-2015_12
Patent number
US09221811B2

Reaction notes

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