반응 #964367

반응 방정식

3-methyl 2-{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}butanoic acid

methyl (2E)-3-(2-aminophenyl)prop-2-enoate

pyridine

O-(7-azabenzotriazol-1-yl)-N,N,N′N′-tetramethyluronium hexafluorophosphate

HATU

→

crude product

Methyl (2E)-3-{2-[(3-methyl-2-{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)-methyl]phenyl}butanoyl)amino]phenyl}prop-2-enoate

용매

DMF

반응 조건

후처리

1. 1
   workup.ADDITIONthe reaction mixture was poured onto ice-water
2. 2
   기타the phases were separated
3. 3
   추출the aqueous phase was extracted three times with tert-butyl methyl ether
4. 4
   건조The combined organic phases were dried over sodium sulfate
5. 5
   여과after filtration the solvent
6. 6
   기타was removed to dryness under reduced pressure

실험 절차

A solution of 50 mg (0.14 mmol) of 3-methyl 2-{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}butanoic acid (enantiomer 2; Example 79A), 20 mg (0.11 mmol) of methyl (2E)-3-(2-aminophenyl)prop-2-enoate, 1.5 ml of pyridine and 65 mg (0.17 mmol) of O-(7-azabenzotriazol-1-yl)-N,N,N′N′-tetramethyluronium hexafluorophosphate (HATU) in 5 ml of DMF was stirred at room temperature overnight. After the reaction had ended, the reaction mixture was poured onto ice-water, the phases were separated and the aqueous phase was extracted three times with tert-butyl methyl ether. The combined organic phases were dried over sodium sulfate, and after filtration the solvent was removed to dryness under reduced pressure. The crude product obtained was purified by preparative HPLC. This gave 7 mg (0.01 mmol, 9.8% of theory) of a colorless oil.

출처