HCID 131723568, compound → HCID 131723567, compound

HRID 1297202Notes

Reaction equation

HRID 1297202 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>C(Cl)Cl.FC(F)(F)C(O)=O>[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 1

HCID 131723568HCID 131723568, compound

Product 1

HCID 131723567HCID 131723567, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Under N2 atmosphere, the Boc-DPro-3-piperidinamide was dissolved in 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. additionadded
  2. stirringThe reaction mixture was stirred for 30 min
  3. customAll volatiles were removed under vacuum
  4. dissolutionthe residue dissolved in 30 ml of CH2Cl2
  5. washwashed with 10 ml saturated NaHCO3 aqueous solution
  6. customThe organic layer was removed
  7. extractionthe aqueous layer extracted with CH2Cl2 (3×10 ml)
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customthe solvent was removed by vacuum
  11. customThe residue was further purified by column chromatography (SiO2, CHCl3/MeOH, 85:15)

Sources & evidence

ORD record
ord-d4db965eadeb420bb3467b02d3d6cbc9
Source dataset
uspto-grants-2007_07
Patent number
US07250399B2

Reaction notes

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