Reaction #6711

ord-71d5c1e5a135455fba4054b6175a1d2a

Reaction equation

CCN(CC)CC
triethylamine
O=C(O)[C@H]1CCCN1C(=O)OCc1ccccc1
Z-D-Pro-OH
CC(C)[C@H](N)C(=O)N(C)[C@H](C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCc1ccccc1)C(C)C
H-Val-MeVal-Pro-Pro-NHBn
Cl
HCl
→
CC(C)[C@H](NC(=O)[C@H]1CCCN1C(=O)OCc1ccccc1)C(=O)N(C)[C@H](C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCc1ccccc1)C(C)C
Z-D-Pro-Val-MeVal-Pro-Pro-NHBn

Reactants

CCN(CC)CC
triethylamine
O=C(O)[C@H]1CCCN1C(=O)OCc1ccccc1
Z-D-Pro-OH
CC(C)[C@H](N)C(=O)N(C)[C@H](C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCc1ccccc1)C(C)C
H-Val-MeVal-Pro-Pro-NHBn
Cl
HCl
—
pentapeptide

Reagents

None

Solvents

CN(C)C=O
DMF

Conditions

Temperature
0°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherthe DMF was evaporated under reduced pressure
  2. 2
    workup.ADDITIONThe residue was diluted with ethyl acetate
  3. 3
    Washthoroughly washed with dilute aqueous HCl (pH 2), water, dilute aqueous NaOH (pH 9–10), and water
  4. 4
    DryingThe organic phase was dried over sodium sulfate
  5. 5
    Otherevaporated to dryness
  6. 6
    Otherto yield 9.2 g of the

Procedure

3.74 g Z-D-Pro-OH (15 mmol, BACHEM) and 8.25 g H-Val-MeVal-Pro-Pro-NHBn×HCl (15 mmol) were dissolved in 80 ml dry DMF. After cooling to 0° C., 2.4 g DEPCN (2.25 ml, 15 mmol) and 4.2 ml triethylamine (30 mmol) were added. The reaction mixture was stirred at 0° C. for several hours and room temperature overnight, then the DMF was evaporated under reduced pressure. The residue was diluted with ethyl acetate and thoroughly washed with dilute aqueous HCl (pH 2), water, dilute aqueous NaOH (pH 9–10), and water. The organic phase was dried over sodium sulfate and evaporated to dryness to yield 9.2 g of the desired protected pentapeptide.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07084110B2uspto-grants-2006_08