HCID 131723570, compound → HCID 131723569, compound

HRID 992410Notes

Reaction equation

HRID 992410 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@@H:2]([C:13]([N:15]1[CH2:22][CH2:21][CH2:20][C@@H:16]1[C:17]([OH:19])=[O:18])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[NH:30]1[CH2:35][CH2:34][CH2:33][CH:32]([C:36](N)=O)[CH2:31]1>C(Cl)Cl>[NH2:1][C@@H:2]([C:13]([N:15]1[CH2:22][CH2:21][CH2:20][C@@H:16]1[C:17]([OH:19])=[O:18])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[CH3:36][CH:32]1[CH2:33][CH2:34][CH2:35][N:30]([C:13]([NH2:15])=[O:14])[CH2:31]1

Participants

3

Reactant 1

HCID 131723570HCID 131723570, compound

Product 1

HCID 131723569HCID 131723569, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under N2 atmosphere, the Boc-DTrp-DPro-3-piperidinamide was dissolved in 25 ml of CH2Cl2 and 10 ml of trifluoracetic was added while being stirred. The reaction mixture was stirred for 30 min. All 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 (3×20 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 0.43 mmol (68.3%) of compound (2) which was characterized by TLC and mass spectra, M+=382.46.

Workup

  1. addition10 ml of trifluoracetic was added
  2. stirringThe reaction mixture was stirred for 30 min
  3. customAll volatiles were removed under vacuum
  4. dissolutionthe residue was 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 was extracted with CH2Cl2 (3×20 ml)
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customthe solvent removed in vacuum
  11. customThe residue was further purified by column chromatography (SiO2, CHCl3/MeOH, 85:15)

Sources & evidence

ORD record
ord-6f6946676bb44ac18938ddbacac311cc
Source dataset
uspto-grants-2002_10
Patent number
US06468974B1

Reaction notes

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