Trifluoroacetic acid → HCID 23433566, compound

HRID 2287356Notes

Reaction equation

HRID 2287356 reaction equation
C(OC([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[CH:16]=2)[CH:11]([CH2:20][CH3:21])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:20]([CH:11]1[C:12]2[C:17](=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[NH:8][CH2:9][CH2:10]1)[CH3:21]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23433550HCID 23433550, compound

Product 1

HCID 23433566HCID 23433566, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an oven dried 250 mL round bottom flask equipped with a magnetic stir bar and a N2 gas inlet was added VI (805 mg, 2.76 mmol) in dry CH2Cl2 (50 mL). To the stirred solution was added TFA (10 mL) at room temperature and was allowed to react for 1 h. The solution was concentrated, quenched with saturated NaHCO3 solution, extracted with CH2Cl2, the organic layer dried (MgSO4), concentrated, and purified via radial chromatography (4 mm plate) on silica gel using hexanes followed by hexanes/ethyl acetate (20/1) to afford VII as a clear colorless oil (509 mg, 2.66 mmol, 96%). Spectral data matched that previously disclosed for this compound.

Workup

  1. customTo an oven dried 250 mL round bottom flask
  2. customequipped with a magnetic stir bar and a N2 gas inlet
  3. customto react for 1 h
  4. concentrationThe solution was concentrated
  5. customquenched with saturated NaHCO3 solution
  6. extractionextracted with CH2Cl2
  7. dry with materialthe organic layer dried (MgSO4)
  8. concentrationconcentrated
  9. custompurified via radial chromatography (4 mm plate) on silica gel

Sources & evidence

ORD record
ord-cf4de5fe742342e79574d9444c418ebd
Source dataset
uspto-grants-2000_07
Patent number
US06083956

Reaction notes

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