Trifluoroacetic acid → HCID 86682831, compound

HRID 526058Notes

Reaction equation

HRID 526058 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]3[N:22]=[C:23]([O:30][C:31]4[CH:36]=[CH:35][CH:34]=[C:33]([NH:37][C:38](=[O:41])[CH:39]=[CH2:40])[CH:32]=4)[C:24]4[S:29][CH:28]=[CH:27][C:25]=4[N:26]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[N:11]1([C:14]2[CH:15]=[CH:16][C:17]([NH:20][C:21]3[N:22]=[C:23]([O:30][C:31]4[CH:32]=[C:33]([NH:37][C:38](=[O:41])[CH:39]=[CH2:40])[CH:34]=[CH:35][CH:36]=4)[C:24]4[S:29][CH:28]=[CH:27][C:25]=4[N:26]=3)=[CH:18][CH:19]=2)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86682832HCID 86682832, compound

Product 1

HCID 86682831HCID 86682831, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound (600 mg, 1.05 mmol) obtained in Step 1 was dissolved in dichloromethane (10 mL), and trifluoroacetic acid (1.62 mL, 21.0 mmol) was added thereto, followed by stirring at room temperature for 1 hour. After the reaction was complete, the reaction mixture was distilled under a reduced pressure to remove solvent, alkalify (pH 8) with sat. NaHCO3 aqueous solution, and extracted with chloroform 2 times. The organic layer was separated, washed with water and sat. brine, dried with anhydrous sodium sulfate, and then filtered and distilled under a reduced pressure. The residue was separated by column chromatography (chloroform:methanol=10:1 (volume ratio)) to obtain the title compound (yield: 316 mg, 72%).

Workup

  1. distillationthe reaction mixture was distilled under a reduced pressure
  2. customto remove solvent, alkalify (pH 8) with sat. NaHCO3 aqueous solution
  3. extractionextracted with chloroform 2 times
  4. customThe organic layer was separated
  5. washwashed with water and sat. brine
  6. dry with materialdried with anhydrous sodium sulfate
  7. filtrationfiltered
  8. distillationdistilled under a reduced pressure
  9. customThe residue was separated by column chromatography (chloroform:methanol=10:1 (volume ratio))

Sources & evidence

ORD record
ord-d9e2ae6c7b8a48fbb047f6e93d8eeb8f
Source dataset
uspto-grants-2016_05
Patent number
US09345719B2

Reaction notes

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