반응 #964366

반응 방정식

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

methyl 3-(3-aminocyclohexyl)propanoate hydrochloride

N,N-diisopropylethylamine

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

→

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

용매

DMF

반응 조건

후처리

1. 1
   workup.ADDITIONthe reaction mixture was poured onto ice-water, whereupon the target compound
2. 2
   기타precipitated in the form of white crystals
3. 3
   여과After filtration
4. 4
   기타the crystals obtained
5. 5
   세척were washed three times with water
6. 6
   기타dried overnight at 40° C. in a vacuum
7. 7
   기타drying cabinet
8. 8
   workup.ADDITIONThis gave 830 mg (1.58 mol, 98% of theory) of the title compound as a mixture of diastereomers

실험 절차

A solution of 590 mg (1.5 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), 400 mg (1.8 mmol) of methyl 3-(3-aminocyclohexyl)propanoate hydrochloride (mixture of isomers), 1.05 ml (6.0 mmol) of N,N-diisopropylethylamine and 857 mg (2.26 mmol) of O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) in 13 ml of DMF was stirred at room temperature overnight. After the reaction had ended, the reaction mixture was poured onto ice-water, whereupon the target compound precipitated in the form of white crystals. After filtration, the crystals obtained were washed three times with water and then dried overnight at 40° C. in a vacuum drying cabinet. This gave 830 mg (1.58 mol, 98% of theory) of the title compound as a mixture of diastereomers.

출처