반응 #325369

반응 방정식

HATU

DIEA

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

tert-butyl 1-(4-aminopentyl)cyclo-propanecarboxylate

→

Tert-Butyl 1-(4-{[2-cyclopentyl-2-{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}acetyl]amino}pentyl)cyclopropanecarboxylate

용매

water

DMF

반응 조건

후처리

1. 1
   온도The reaction mixture was slowly warmed to RT
2. 2
   추출extracted three times with ethyl acetate
3. 3
   건조The combined organic phases were dried over magnesium sulfate
4. 4
   농축concentrated under reduced pressure
5. 5
   기타Purification of the crude product by preparative RP-HPLC (acetonitrile/water gradient)
6. 6
   기타gave 540.0 mg (68.0% of theory) of the target compound as a diastereomer mixture

실험 절차

At RT, 253 μl (1.45 mmol) of DIEA were added to a solution of 517.9 mg (1.32 mmol) of (+)-cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}acetic acid and 450 mg (about 1.98 mmol, crude material) of tert-butyl 1-(4-aminopentyl)cyclo-propanecarboxylate in 2.5 ml of DMF. The resulting mixture was cooled to 0° C., and four portions of altogether 186.4 mg (0.49 mmol) of HATU were then added. The reaction mixture was slowly warmed to RT, stirred at RT for 16 h and then added to water and extracted three times with ethyl acetate. The combined organic phases were dried over magnesium sulfate and concentrated under reduced pressure. Purification of the crude product by preparative RP-HPLC (acetonitrile/water gradient) gave 540.0 mg (68.0% of theory) of the target compound as a diastereomer mixture.

출처