反応 #2069938

反応方程式

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

収率 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

収率 93.0%

溶媒

THF

THF

DCM

DMF

ethyl acetate cyclohexane

DCM

反応条件

後処理

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

実験手順

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.

出典