Trifluoroacetic acid → HCID 44129711, compound

HRID 1693248Notes

Reaction equation

HRID 1693248 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]([NH:17][C:18]2[CH:19]=[CH:20][C:21]([F:42])=[C:22]([C@:24]34[CH2:33][CH2:32][CH2:31][CH2:30][C@H:29]3[CH2:28][S:27][C:26]([NH:34]C(=O)OC(C)(C)C)=[N:25]4)[CH:23]=2)=[O:16])=[N:13][CH:14]=1.C(=O)(O)[O-].[Na+]>ClCCl.C(OCC)C>[NH2:34][C:26]1[S:27][CH2:28][C@@H:29]2[CH2:30][CH2:31][CH2:32][CH2:33][C@:24]2([C:22]2[CH:23]=[C:18]([NH:17][C:15]([C:12]3[CH:11]=[CH:10][C:9]([Cl:8])=[CH:14][N:13]=3)=[O:16])[CH:19]=[CH:20][C:21]=2[F:42])[N:25]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 89737682HCID 89737682, compound

Product 1

HCID 44129711HCID 44129711, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (200 μL) was added to a solution of the compound of Example 1 (23.0 mg) in dichloromethane (1.00 mL), and the mixture was stirred at room temperature for four hours. The reaction solution was diluted with diethyl ether and neutralized with a sodium bicarbonate solution. The reaction mixture was extracted with ethyl acetate, and the organic layer was washed with a saturated sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure to obtain a residue. The residue was purified by NH-silica gel column chromatography to obtain the title compound (18.0 mg).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with a saturated sodium chloride solution
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customThe drying agent was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customto obtain a residue
  7. customThe residue was purified by NH-silica gel column chromatography

Sources & evidence

ORD record
ord-03ea8330963846ab840763fd04367052
Source dataset
uspto-grants-2012_04
Patent number
US08158620B2

Reaction notes

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