Reaction #969872

Reaction equation

Boc-Val-Pro-OH

1-hydroxibenzotriazol

N,N-diisopropylcarbodiimide

Ara-C

→

Ara-C-dipeptide

Yield 21.0%

Boc-Val-Pro Ara-C

Yield 21.0%

Solvents

dimethylformamide

Conditions

Workup

1. 1
   OtherThen, the solvent was evaporated
2. 2
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
3. 3
   Washwashed with citric acid (10%), NaHCO3 (10%) and brine
4. 4
   DryingThe organic layer was dried (Na2SO4)
5. 5
   Otherevaporated
6. 6
   Otherto give a residue that
7. 7
   Otherwas purified by CCTLC on the chromatotron with dichloromethane:methanol (20:1)

Procedure

A solution of Boc-Val-Pro-OH (94.5 mg, 0.30 mmol) in dimethylformamide (1.5 mL), was successively treated, at room temperature, with 1-hydroxibenzotriazol (40.5 mg, 0.30 mmol), N,N-diisopropylcarbodiimide (46.7 μL, 0.30 mmol) and Ara-C (60.9 mg, 0.25 mmol). The stirring was continued until complete disappearance of the starting material (overnight stirring). Then, the solvent was evaporated, the residue was dissolved in ethyl acetate and washed with citric acid (10%), NaHCO3 (10%) and brine. The organic layer was dried (Na2SO4) and evaporated to give a residue that was purified by CCTLC on the chromatotron with dichloromethane:methanol (20:1) to yield Ara-C-dipeptide (A) (21% yield)

Source