반응 #964360

반응 방정식

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

methyl 4-amino-2-methyl-2,3-dihydro-1H-indene-2-carboxylate

Methyl 4-amino-2-methyl-2,3-dihydro-1H-indene-2-carboxylate

pyridine

→

crude product

Methyl 4-[(cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]-phenyl}acetyl)amino]-2-methyl-2,3-dihydro-1H-indene-2-carboxylate

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 200 mg (0.97 mmol) of cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}acetic acid (enantiomer 2, Example 77A), 459 mg (1.2 mmol) of methyl 4-amino-2-methyl-2,3-dihydro-1H-indene-2-carboxylate (Example 95A), 556 mg (1.46 mmol) of O-(7-azabenzotriazol-1-yl)-N,N,N′N′-tetramethyluronium hexafluorophosphate (HATU) and 5 ml of pyridine in 20 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 448 mg (0.77 mmol, 79% of theory) of a colorless oil.

출처