Réaction #2069938

Équation de réaction

3-amino-4,6-dihydro-pyrrolo[3,4-c]pyrazole-1,5-dicarboxylic acid 5-tert-butyl ester 1-ethyl ester

DIEA

(COCl)2

2-naphthalen-2-yl-propionic acid

→

title compound

Rendement 93.0%

3-(2-Naphthalen-2-yl-propionylamino)-4,6-dihydro-pyrrolo[3,4-c]pyrazole-1,5-dicarboxylic acid 5-tert-butyl ester 1-ethyl ester

Rendement 93.0%

Solvants

THF

THF

DCM

DMF

ethyl acetate cyclohexane

DCM

Conditions de réaction

Traitement

1. 1
   ConcentrationThe reaction mixture was concentrated under vacuum
2. 2
   Concentrationconcentrated
3. 3
   Autreto reach r.t.
4. 4
   workup.STIRRINGstirred overnight
5. 5
   FiltrationThe mixture was filtered
6. 6
   Autrethe solution evaporated to dryness under vacuum
7. 7
   workup.DISSOLUTIONThe resulting residue was dissolved in DCM
8. 8
   Lavagethe obtained solution was washed with brine
9. 9
   Séchagedried over sodium sulfate
10. 10
    Filtrationfiltered
11. 11
    Autreevaporated to dryness
12. 12
    AutreThe crude product was purified by flash-chromatography (eluent

Mode opératoire

To a solution of 2-naphthalen-2-yl-propionic acid (1.48 g. 7.4 mmol) in DCM (40 ml) and DMF cat., (COCl)2 (0.83 ml, 9.65 mmol) in DCM (10 ml) was added dropwise. The mixture was stirred at r.t. for 30 min. The reaction mixture was concentrated under vacuum, reconstituted twice with toluene and concentrated. A solution of the obtained acyl-chloride in THF (40 ml) was added slowly to a mixture of 3-amino-4,6-dihydro-pyrrolo[3,4-c]pyrazole-1,5-dicarboxylic acid 5-tert-butyl ester 1-ethyl ester (2.0 g, 6.75 mmol) and DIEA (5.8 ml, 33.3 mmol) in THF (40 ml) at 0-5° C. The reaction was allowed to reach r.t. and stirred overnight. The mixture was filtered and the solution evaporated to dryness under vacuum. The resulting residue was dissolved in DCM and the obtained solution was washed with brine, dried over sodium sulfate, filtered and evaporated to dryness. The crude product was purified by flash-chromatography (eluent:ethyl acetate/cyclohexane 3/7 then 4/6) to give 3.0 g (93% yield) of the title compound as a white solid.

Source