Trifluoroacetic acid → HCID 66645881, compound

HRID 1694940Notes

Reaction equation

HRID 1694940 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][C:19](=[O:21])[N:18]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:23]=2[CH3:29])[CH2:17][C:16]1([CH3:31])[CH3:30])=O)(C)(C)C>C(Cl)Cl>[CH3:30][C:16]1([CH3:31])[CH2:17][N:18]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:23]=2[CH3:29])[C:19](=[O:21])[CH2:20][NH:15]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66645797HCID 66645797, compound

Product 1

HCID 66645881HCID 66645881, compoundYield 102.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.8 ml of trifluoroacetic acid (37 mmol) was added to a solution of 1.25 g of 2,2-dimethyl-4-(3-fluoro-2-methylphenyl)-5-oxopiperazine-1-carboxylic acid t-butyl ester obtained in Example (67c) (3.7 mmol) in methylene chloride (5.6 ml) at room temperature, and the mixture was stirred at the same temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure. A saturated sodium bicarbonate aqueous solution was added, followed by extraction with methylene chloride. Then, the organic layer was dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent:methylene chloride/methanol=10/1) to obtain 0.9 g of the title compound (yield: quant.).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionA saturated sodium bicarbonate aqueous solution was added
  3. extractionfollowed by extraction with methylene chloride
  4. dry with materialThen, the organic layer was dried 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 (elution solvent:methylene chloride/methanol=10/1)

Sources & evidence

ORD record
ord-fce9faa7a6d8467caedf6a1447279fd4
Source dataset
uspto-grants-2012_04
Patent number
US08158790B2

Reaction notes

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