Reacción #969866

Ecuación de reacción

phenylalanine

Et3N

diallyl glutamate

triphosgene

Et3N

→

ninhydrin

Disolventes

CH2Cl2

CH2Cl2

CH2Cl2

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe reaction was stirred at room temperature for 12 h
2. 2
   Lavadowashed twice with H2O
3. 3
   Secadodried over MgSO4 (anh.)
4. 4
   Otropurified by column chromatography (Hexane:AcOEt 3:1)

Procedimiento

To a stirred solution of diallyl glutamate (110 mg, 0.42 mmol) and triphosgene (43 mg, 0.14 mmol) in CH2Cl2 (4 mL) at −78° C. was added Et3N (180 μL, 1.3 mmol) in CH2Cl2 (0.8 mL). The reaction mixture was allowed to warm to room temperature and stirred for 1.5 h. The phenylalanine derivative (140 mg, 0.251 mmol) in a solution of CH2Cl2 (1 mL) and Et3N (70 μL, 0.5 mmol) was then added at −78° C. and the reaction was stirred at room temperature for 12 h. The solution was diluted with CH2Cl2, washed twice with H2O, dried over MgSO4 (anh.) and purified by column chromatography (Hexane:AcOEt 3:1) to give 100 mg (57%) (TLC in CH2Cl2:MeOH 20:1 Rf=0.3, revealed with ninhydrin and uv light). 1H-NMR (CDCl3, 300 MHz) δ 7.80-6.95 (13H, aromatics, NHFmoc), 5.98-5.82 (m, 3H, 3-CH2CHCH2), 5.54 (bd, 1H, NHurea), 5.43-5.19 (m, 7H, 3-CH2CHCH2, NHurea), 4.85-4.78 (m, 1H, CH(pheala.)), 4.67-4.50 (m, 9H, 3-CH2CHCH2, CH2(Fmoc), CH(glu.)), 4.28 (t, 1H, CH(Fmoc)), 3.05 (d, 2H, CH2(pheala.)), 2.53-2.33 (m, 2H, CH2(glu.)), 2.25-2.11 and 1.98-1.80 (2m, 2H, CH2(glu.)).

Fuente