Trifluoroacetic acid → HCID 131723567, compound

HRID 992409Notes

Reaction equation

HRID 992409 reaction equation
[N:1]1([C:9](OC(C)(C)C)=[O:10])[CH2:8][CH2:7][CH2:6][C@@H:2]1[C:3]([OH:5])=[O:4].[NH:16]1[CH2:21][CH2:20][CH2:19][CH:18]([C:22](N)=O)[CH2:17]1.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].[CH3:22][CH:18]1[CH2:19][CH2:20][CH2:21][N:16]([C:9]([NH2:1])=[O:10])[CH2:17]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131723568HCID 131723568, compound

Product 1

HCID 131723567HCID 131723567, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under N2 atmosphere, the Boc-DPro-3-piperidinamide was dissolved in 25 ml of CH2Cl2 and 10 ml of trifluoracetic acid added while stirring. The reaction mixture was stirred for 30 min. All volatiles were removed under vacuum and the residue dissolved in 30 ml of CH2Cl2 and washed with 10 ml saturated NaHCO3 aqueous solution. The organic layer was removed and the aqueous layer extracted with CH2Cl2 (3×10 ml). The organic layer was dried over anhydrous sodium sulfate and filtered and the solvent was removed by vacuum. The residue was further purified by column chromatography (SiO2, CHCl3/MeOH, 85:15) to afford 0.65 mmol (65%) of compound (1) which was characterized by TLC and mass spectra, M+=196.3.

Workup

  1. stirringThe reaction mixture was stirred for 30 min
  2. customAll volatiles were removed under vacuum
  3. dissolutionthe residue 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 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 by vacuum
  10. customThe residue was further purified by column chromatography (SiO2, CHCl3/MeOH, 85:15)

Sources & evidence

ORD record
ord-a4e3ee279c2743e18172c9662fd5ecea
Source dataset
uspto-grants-2002_10
Patent number
US06468974B1

Reaction notes

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