Trifluoroacetic acid → HCID 131723572, compound

HRID 1297205Notes

Reaction equation

HRID 1297205 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C:2]([C:5]([NH:7][C@@H:8]([C:19]([N:21]1[CH2:28][CH2:27][CH2:26][C@@H:22]1[C:23]([OH:25])=[O:24])=[O:20])[CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]=1)=[O:6])([CH3:4])[CH3:3].[NH:36]1[CH2:41][CH2:40][CH2:39][CH:38]([C:42](N)=O)[CH2:37]1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:1][C:2]([C:5]([NH:7][C@@H:8]([C:19]([N:21]1[CH2:28][CH2:27][CH2:26][C@@H:22]1[C:23]([OH:25])=[O:24])=[O:20])[CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]=1)=[O:6])([CH3:3])[CH3:4].[CH3:42][CH:38]1[CH2:39][CH2:40][CH2:41][N:36]([C:5]([NH2:7])=[O:6])[CH2:37]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131723571HCID 131723571, compound

Product 1

HCID 131723572HCID 131723572, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under N2 atmosphere, the Boc-Aib-DTrp-DPro-3-piperidinamide was dissolved in 25 ml of CH2Cl2 and 10 ml of trifluoracetic acid was added while being stirred. The reaction mixture was stirred for 30 min. Al volatiles were removed under vacuum and the residue was dissolved in 30 ml of CH2Cl2 and washed with 10 ml saturated NaCHO3 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, filtered and the solvent removed in vacuum. The residue was further purified by column chromatography (SiO2, CHCl3/MeOH, 85:15) to afford 0.28 mmol (84.8%) of compound (YL-111) which was characterized by TLC and mass spectra M+=468.6.

Workup

  1. stirringThe reaction mixture was stirred for 30 min
  2. customAl volatiles were removed under vacuum
  3. dissolutionthe residue was dissolved in 30 ml of CH2Cl2
  4. washwashed with 10 ml saturated NaCHO3 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 removed in vacuum
  10. customThe residue was further purified by column chromatography (SiO2, CHCl3/MeOH, 85:15)

Sources & evidence

ORD record
ord-b7fe85e5429848c18dececc10c995179
Source dataset
uspto-grants-2007_07
Patent number
US07250399B2

Reaction notes

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