Reacción #2069938

Ecuación de reacción

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

Rendimiento 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

Rendimiento 93.0%

Disolventes

THF

THF

DCM

DMF

ethyl acetate cyclohexane

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónThe reaction mixture was concentrated under vacuum
2. 2
   Concentraciónconcentrated
3. 3
   Otroto reach r.t.
4. 4
   workup.STIRRINGstirred overnight
5. 5
   FiltraciónThe mixture was filtered
6. 6
   Otrothe solution evaporated to dryness under vacuum
7. 7
   workup.DISSOLUTIONThe resulting residue was dissolved in DCM
8. 8
   Lavadothe obtained solution was washed with brine
9. 9
   Secadodried over sodium sulfate
10. 10
    Filtraciónfiltered
11. 11
    Otroevaporated to dryness
12. 12
    OtroThe crude product was purified by flash-chromatography (eluent

Procedimiento

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.

Fuente