Trifluoroacetic acid → HCID 57736457, compound

HRID 1641729Notes

Reaction equation

HRID 1641729 reaction equation
C([O:5][C:6](=O)[NH:7][CH2:8][CH2:9][NH:10][C:11]([C:13]1[CH:18]=[C:17]([CH3:19])[C:16]([CH:20]([C:31]2C=C(F)[CH:34]=[CH:33][C:32]=2[F:38])[S:21]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)(=[O:23])=[O:22])=[CH:15][N:14]=1)=[O:12])(C)(C)C.[C:40](OC(=O)C)(=O)C.C(N(CC)CC)C.F[C:55]([F:60])(F)[C:56](O)=O>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:6]([NH:7][CH2:8][CH2:9][NH:10][C:11]([C:13]1[CH:18]=[C:17]([CH3:19])[C:16]([CH:20]([C:31]2[CH:56]=[C:55]([F:60])[CH:34]=[CH:33][C:32]=2[F:38])[S:21]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)(=[O:22])=[O:23])=[CH:15][N:14]=1)=[O:12])(=[O:5])[CH3:40]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 57736512HCID 57736512, compound

Product 1

HCID 57736457HCID 57736457, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl[2-[[[5-[(2,5-difluorophenyl) [(4-fluorophenyl)sulfonyl]meth yl]-4-methylpyridin-2-yl]carbonyl]amino]ethyl]carbamate (90 mg, 0.160 mmol) in methylene chloride (5 ml), trifluoroacetic acid (2 ml) was added, and the resulting mixture was stirred for 2.5 hours at room temperature. The reaction solution was concentrated under reduced pressure, and methylene chloride and a 0.5 N aqueous sodium hydroxide were added thereto. The organic layer was separated, dried over anhydrous sodium sulfate, and filtered, and then the filtrate was concentrated under reduced pressure. The resulting concentration residue was dissolved in methylene chloride (5 ml), and acetic anhydride (23 μl, 0.240 mmol), triethylamine (26 μl, 0.240 mmol) and a catalytic amount of 4-dimethylaminopyridine were added thereto. The reaction solution was stirred for 20 hours at room temperature, and was concentrated under reduced pressure. The resulting concentration residue was subjected to silica gel column chromatography, and the fraction obtained from an elution with methanol:methylene chloride (=1:20) was concentrated under reduced pressure, to obtain the title compound (79 mg, 0.156 mmol, 98%) as an amorphous substance.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure, and methylene chloride
  2. additiona 0.5 N aqueous sodium hydroxide were added
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. concentrationThe resulting concentration residue
  8. dissolutionwas dissolved in methylene chloride (5 ml)
  9. stirringThe reaction solution was stirred for 20 hours at room temperature
  10. concentrationwas concentrated under reduced pressure
  11. concentrationThe resulting concentration residue
  12. customthe fraction obtained from an elution with methanol
  13. concentrationmethylene chloride (=1:20) was concentrated under reduced pressure

Sources & evidence

ORD record
ord-079ef149219b466189176fdeef2209f1
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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