Trifluoroacetic acid → HCID 21948309, compound

HRID 2214811Notes

Reaction equation

HRID 2214811 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:15][C:16]([N:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]2([C:38]([O:40]C(C)(C)C)=[O:39])[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]2)[C:20](=[O:45])[CH2:19]1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1(C)C=CC=CC=1>[CH2:8]([O:15][C:16]([N:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]2([C:38]([OH:40])=[O:39])[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:36])([CH3:37])[CH3:35])=[O:32])[CH2:27][CH2:26]2)[C:20](=[O:45])[CH2:19]1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 12071176HCID 12071176, compound

Product 1

HCID 21948309HCID 21948309, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Trifluoroacetic acid (100 ml) was added to a solution of 4-benzyloxycarbonyl-1-[1,4-bis(tert-butoxycarbonyl)-4-piperidylmethyl]-2-piperazinone (38.8 g) obtained in Reference Example 1 in toluene (100 ml), the mixture was stirred at room temperature for 1 hour, and concentrated under reduced pressure. Then, di-tert-butyl dicarbonate (17.6 ml) was added to a mixture of the residue, sodium carbonate (38.7 g), water (300 ml) and ethyl acetate (300 ml) at room temperature while stirring, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was separated into layers, the aqueous layer was adjusted to pH 3 with 1N hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate layer was dried with magnesium sulfate, and concentrated under reduced pressure, and the residue was purified by silica gel chromatography (ethyl acetate:methanol=10/1) to obtain the title compound (29 g) as yellow powders.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThen, di-tert-butyl dicarbonate (17.6 ml) was added to a mixture of the residue, sodium carbonate (38.7 g), water (300 ml) and ethyl acetate (300 ml) at room temperature
  3. stirringwhile stirring
  4. stirringthe mixture was stirred at room temperature for 1 hour
  5. customThe reaction mixture was separated into layers
  6. extractionextracted with ethyl acetate
  7. dry with materialThe ethyl acetate layer was dried with magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customthe residue was purified by silica gel chromatography (ethyl acetate:methanol=10/1)

Sources & evidence

ORD record
ord-a87c728423544d99b4916c2cdaaac2a7
Source dataset
uspto-grants-2006_09
Patent number
US07109200B2

Reaction notes

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