Trifluoroacetic acid → HCID 131723559, compound

HRID 1297198Notes

Reaction equation

HRID 1297198 reaction equation
[N:1]1(C(OC(C)(C)C)=O)[CH2:8][CH2:7][CH2:6][C@@H:2]1[C:3]([OH:5])=[O:4].[CH2:16]([N-:20][CH2:21][CH:22]([CH3:24])[CH3:23])[CH:17]([CH3:19])[CH3:18].FC(F)(F)C(O)=O>C(Cl)Cl>[NH:1]1[CH2:8][CH2:7][CH2:6][C@@H:2]1[C:3]([OH:5])=[O:4].[CH2:16]([N-:20][CH2:21][CH:22]([CH3:24])[CH3:23])[CH:17]([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131723560HCID 131723560, compound

Product 1

HCID 131723559HCID 131723559, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under N2 atmosphere, the Boc-DPro-diisobutylamide was dissolved in 25 ml of CH2Cl2 and 1-ml of trifluoracetic acid was added while being stirred. The reaction mixture was stirred for 30 min. Volatiles were removed under vacuum and the residue was dissolved in 30 ml of CH2Cl2 and washed with 10 ml saturated NaHCO3 aqueous solution. The organic layer was removed and the aqueous layer was extracted with CH2Cl2 (3×10 ml). The organic layer was dried over anhydrous sodium sulfate and filtered and the solvent was removed in vacuum. The residue was further purified by column chromatography (SiO2, CHCl3/MeOH, 85:15) to afford 0.73 mmol (73%) of compound (1) which was characterized by TLC on mass spectra, M+=225.1.

Workup

  1. stirringThe reaction mixture was stirred for 30 min
  2. customVolatiles were removed under vacuum
  3. dissolutionthe residue was dissolved in 30 ml of CH2Cl2
  4. washwashed with 10 ml saturated NaHCO3 aqueous solution
  5. customThe organic layer was removed
  6. extractionthe aqueous layer was extracted with CH2Cl2 (3×10 ml)
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customthe solvent was removed in vacuum
  10. customThe residue was further purified by column chromatography (SiO2, CHCl3/MeOH, 85:15)

Sources & evidence

ORD record
ord-0d6f4ec3cade4d8699a758afc1e810e1
Source dataset
uspto-grants-2007_07
Patent number
US07250399B2

Reaction notes

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