反应 #2069938

反应方程式

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

收率 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

收率 93.0%

溶剂

THF

THF

DCM

DMF

ethyl acetate cyclohexane

DCM

反应条件

后处理

1. 1
   浓缩The reaction mixture was concentrated under vacuum
2. 2
   浓缩concentrated
3. 3
   其他to reach r.t.
4. 4
   workup.STIRRINGstirred overnight
5. 5
   过滤The mixture was filtered
6. 6
   其他the solution evaporated to dryness under vacuum
7. 7
   workup.DISSOLUTIONThe resulting residue was dissolved in DCM
8. 8
   洗涤the obtained solution was washed with brine
9. 9
   干燥dried over sodium sulfate
10. 10
    过滤filtered
11. 11
    其他evaporated to dryness
12. 12
    其他The crude product was purified by flash-chromatography (eluent

实验过程

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.

来源