HCID 131723243, compound → HCID 58726315, compound

HRID 2184653Notes

Reaction equation

HRID 2184653 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:10]([N:12]1[CH2:23][CH2:22][CH2:21][C@@H:13]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)(=O)C.[Pd]>[NH2:1][C@H:2]([C:10]([N:12]1[CH2:23][CH2:22][CH2:21][C@@H:13]1[C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 131723243HCID 131723243, compound

Product 1

HCID 58726315HCID 58726315, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

The dipeptide compound Z-Phe-D-Pro-OtBu (700 mg, 1.45 mmol) obtained in step 1-1 was dissolved in acetic acid (5 ml) and stirred overnight (about 14 hours) under hydrogen atmosphere in the presence of 5% Pd/C (70 mg). After the reaction mixture was filtered and concentrated, an oily residue was dissolved in ethyl acetate and washed with 4% NaHCO3. After being dried over anhydrous sodium carbonate, the product was concentrated to yield H-Phe-D-Pro-OtBu (425 mg, 92%). The concentrate was redissolved in DMF (5 ml), and Z-Phe-OH (434 mg, 1.45 mmol) and HOBt. H2O (245 mg, 1.60 mmol) were added, followed by adding DCC (230 mg, 1.60 mmol) under ice cooling, and as such the mixture was stirred overnight. The reaction mixture was filtered, concentrated, redissolved in ethyl acetate, and washed sequentially with 10% citric acid, 4% NaHCO3 and with saturated aqueous sodium chloride solution. After being dried over MgSO4 and concentrated, the residue was purified by flash silica gel chromatography (CHCl3) to yield 720 mg (90%) of the titled tripeptide compound as a foamy material.

Workup

  1. filtrationAfter the reaction mixture was filtered
  2. concentrationconcentrated
  3. dissolutionan oily residue was dissolved in ethyl acetate
  4. washwashed with 4% NaHCO3
  5. dry with materialAfter being dried over anhydrous sodium carbonate
  6. concentrationthe product was concentrated

Sources & evidence

ORD record
ord-449212b5fa624f299a54a49026277510
Source dataset
uspto-grants-2002_06
Patent number
US06399568B1

Reaction notes

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