HCID 131722746, compound → HCID 131722745, compound

HRID 1383729Notes

Reaction equation

HRID 1383729 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:10]([NH:12][C@H:13]([C:21]([NH:23][C@H:24]([C:36]([NH2:38])=[O:37])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH:27]=1)=[O:22])[CH2:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[H][H]>CO.[C].[Pd]>[NH2:1][C@H:2]([C:10]([NH:12][C@H:13]([C:21]([NH:23][C@H:24]([C:36]([NH2:38])=[O:37])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([CH3:35])([CH3:33])[CH3:34])[CH:27]=1)=[O:22])[CH2:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 131722746HCID 131722746, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131722745HCID 131722745, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 188 mg (0.287 mmol) of Z-Phe-Cha-Phe(3-tBu)-NH2 in 3 ml of methanol, 100 mg of 10% palladium carbon was added and the mixture was stirred overnight in a hydrogen atmosphere at room temperature. After filtering, the filtrate was concentrated under reduced pressure and the resulting residue was subjected to silica gel column chromatography (eluting solvent, chloroform:methanol=10:1) to yield Phe-Cha-Phe(3-tBu)-NH2 in the amount of 69.0 mg (46%).

Workup

  1. filtrationAfter filtering
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. washthe resulting residue was subjected to silica gel column chromatography (eluting solvent, chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-3a30de02681246cc8dbc4946d0a01b3a
Source dataset
uspto-grants-2001_07
Patent number
US06255285B1

Reaction notes

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