Reaction #7420

Reaction equation

Example 1

tert-Butyl(2R)-2-((3R)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoate

chloroethylmorpholine hydrochloride

potassium carbonate

ethyl acetate

DMF

→

title compound

6-Chloro-N-{(3S)-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-yl}-N-(2-morpholin-4-ylethyl)naphthalene-2-sulfonamide formate

Solvents

water

Conditions

Workup

1. 1
   TemperatureThe mixture was then heated at 80° C. for 8 h
2. 2
   Temperaturecooled
3. 3
   DryingThe organic extraxt was dried (over magnesium sulphate)
4. 4
   Concentrationconcentrated under reduced pressure
5. 5
   OtherThe residue was purified

Procedure

Example 1 (0.05 g) was dissolved in DMF (1 ml) and treated with chloroethylmorpholine hydrochloride (0.062 g) and potassium carbonate (0.093 g), and stirred at 40° C. for 2 h. The mixture was then heated at 80° C. for 8 h, cooled and treated with ethyl acetate and water. The organic extraxt was dried (over magnesium sulphate) and concentrated under reduced pressure. The residue was purified using mass directed preparative h.p.l.c. to give the title compound (0.018 g) as a white solid.

Source