Reacción #3191

Ecuación de reacción

3,4-Diethylpyrrole

2-acetoxymethyl-5-benzyloxycarbonyl-4-methyl-3-methoxycarbonylethylpyrrole

p-Toluenesulfonic acid

→

powder

Rendimiento 61.0%

2,5-Bis[(5-benzyloxycarbonyl-4-methyl-3-methoxycarbonylethylpyrrol-2-yl)methyl]-3,4-diethylpyrrole

Rendimiento 61.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroIn a 500 mL round bottom flask was placed
2. 2
   Otro250 mL of ethanol from an unopened bottle and this was then purged with dry nitrogen for ten minutes
3. 3
   workup.DISSOLUTIONdissolved
4. 4
   OtroThe reaction slowly changed color from a clear yellow to a dark red with the product
5. 5
   Otroprecipitating out of the solution as the reaction
6. 6
   TemperaturaAfter ten hours the reaction was cooled to room temperature
7. 7
   Otrothe volume reduced to one half on a rotary evaporator
8. 8
   workup.WAITplaced in the freezer for several hours
9. 9
   FiltraciónThe product was collected by filtration
10. 10
    Lavadowashed with a small amount of cold ethanol

Procedimiento

7C, FIG. 7. In a 500 mL round bottom flask was placed 250 mL of ethanol from an unopened bottle and this was then purged with dry nitrogen for ten minutes. 3,4-Diethylpyrrole 7B (1.29 g, 0.01 mol) and 2-acetoxymethyl-5-benzyloxycarbonyl-4-methyl-3-methoxycarbonylethylpyrrole 7A (7.83 g, 0.02 mol) were added and the mixture heated until all of the pyrroles dissolved. p-Toluenesulfonic acid (65 mg) was added and the reaction temperature maintained at 60° C. The reaction slowly changed color from a clear yellow to a dark red with the product precipitating out of the solution as the reaction progressed. After ten hours the reaction was cooled to room temperature, the volume reduced to one half on a rotary evaporator, and then placed in the freezer for several hours. The product was collected by filtration, washed with a small amount of cold ethanol to afford 4.61 g of an off white fine powder (61%): 1H NMR (CDCl3, 250 MHz): δ1.14 (6H, t, CH2 CH3), 2.23 (6H, s, pyrrole-CH3), 2.31 (4H, t, CH2CH2 CO2CH 3), 2.50 (4H, q, CH2CH3), 2.64 (4H, t, CH2CH2CO2CH3), 3.60 (10H, br s, CH3CO2 -- and (pyrrole)2 --CH2), 4.44 (4H, br s, C6H5 CH2), 6.99-7.02 (4H, m, aromatic), 7.22-7.26 (6H, m, aromatic), 8.72 (1H, s, NH), 10.88 (2H, br s, NH); 13C NMR (CDCl3, 250 MHz): δ10.97, 16.78, 17.71, 19.40, 22.07, 35.09, 51.46, 65.32, 117.37, 119.34, 122.14, 126.58, 126.79, 127.36, 128.19, 133.55, 136.62, 162.35, 173.49; CI MS (M+H)+ 750; HRMS 749.3676 (calc. for C44H51 N3O8 : 749.3676).

Fuente