HCID 54407228, compound → HCID 22854679, compound

HRID 1648121Notes

Reaction equation

HRID 1648121 reaction equation
C([O:5][C:6](=[O:48])[CH2:7][CH:8]([NH:20][C:21](=[O:47])[C@H:22]([CH3:46])[NH:23][C:24](=[O:45])[C@H:25]([CH:42]([CH3:44])[CH3:43])[NH:26][C:27](=[O:41])[C@H:28]([CH2:33][C:34]1[CH:39]=[CH:38][C:37]([OH:40])=[CH:36][CH:35]=1)[NH:29][C:30](=[O:32])[CH3:31])[CH:9]([OH:19])[CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(C)(C)C>C(Cl)Cl.C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-][Cr](O[Cr]([O-])(=O)=O)(=O)=O>[C:30]([NH:29][C@H:28]([C:27]([NH:26][C@H:25]([C:24]([NH:23][C@H:22]([C:21]([NH:20][CH:8]([C:9](=[O:19])[CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH2:7][C:6]([OH:48])=[O:5])=[O:47])[CH3:46])=[O:45])[CH:42]([CH3:44])[CH3:43])=[O:41])[CH2:33][C:34]1[CH:39]=[CH:38][C:37]([OH:40])=[CH:36][CH:35]=1)(=[O:32])[CH3:31]

Participants

4

Reactant 1

HCID 54407228HCID 54407228, compound

Product 1

HCID 22854679HCID 22854679, compoundYield 46.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 2724130Cornforth reagentSolvent

Procedure

N-(N-Acetyl-Tyrosinyl-Valinyl-Alaninyl)-3-amino-4-hydroxy-7-phenyl heptanoic acid t-butyl ester (166 mg, 0.0991 mmol), was dissolved in CH2Cl2 (5 mL) and PDC (56 mg, 0.149 mmoL), was added. The resulting mixture was stirred at rt for 6h. The mixture was filtered through Celite and the solvent was concentrated in vacuo. The residue was chromatographed over silica (95:5, CH2Cl2 :MeOH) to provide the ketone (28 mg) and S.M (33 mg).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe solvent was concentrated in vacuo
  3. customThe residue was chromatographed over silica (95:5, CH2Cl2 :MeOH)

Sources & evidence

ORD record
ord-17cd868a24f24ecebecb4b903ac3255e
Source dataset
uspto-grants-1995_07
Patent number
US05434248

Reaction notes

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