Reaction #969874

ord-da042871c6a0448daa49d5d6ff450a0a

Reaction equation

CC(C)[C@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(=O)N1CCC[C@H]1C(=O)O.Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)c(=O)n1
( D )
CC(C)[C@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(=O)N1CCC[C@H]1C(=O)O.Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)c(=O)n1
Z-Val-Pro-Val-Pro Ara-C
→
CC(C)[C@H](N)C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)O)C(C)C.Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)c(=O)n1
H-Val-Pro-Val-Pro Ara-C
Yield 90.0%

Reactants

—
Ara-C-tetrapeptide-Z
CC(C)[C@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(=O)N1CCC[C@H]1C(=O)O.Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)c(=O)n1
( D )
CC(C)[C@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(=O)N1CCC[C@H]1C(=O)O.Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)c(=O)n1
Z-Val-Pro-Val-Pro Ara-C

Reagents

[Pd]
Pd/C

Solvents

CO
methanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    FiltrationThe reaction mixture was filtered
  2. 2
    Otherthe filtrate was evaporated to dryness, under reduced pressure
  3. 3
    Otherto give D (90% yield)

Procedure

A solution of the corresponding Ara-C-tetrapeptide-Z-protected (D) (24.7 mg, 0.03 mmol) in methanol containing Pd/C (10% wt/wt) (11.5 mg) was hydrogenated at 25 psi at room temperature for 2 h. The reaction mixture was filtered, and the filtrate was evaporated to dryness, under reduced pressure, to give D (90% yield).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08236756B2uspto-grants-2012_08