反応 #157182

反応方程式

(3aR,7aS)-tert-butyl 5-(3-aminopyridin-4-yl)-2-oxohexahydrooxazolo[4,5-c]pyridine-3(2H)-carboxylate

3-amino-6-(2,6-difluorophenyl)picolinic acid

EDC

HOAt

→

(3aR,7aS)-tert-butyl 5-(3-(3-amino-6-(2,6-difluorophenyl)picolinamido)-pyridin-4-yl)-2-oxohexahydrooxazolo[4,5-c]pyridine-3(2H)-carboxylate

収率 46.0%

溶媒

water

DMF

反応条件

後処理

1. 1
   ろ過the precipitate was filtered
2. 2
   workup.ADDITIONTo the filtrate was added EtOAc
3. 3
   抽出the organic solution was extracted (3 times)
4. 4
   乾燥dried with Na2SO4
5. 5
   濃縮concentrated
6. 6
   その他to give an orange syrup
7. 7
   その他The crude was triturated with EtOAc and hexanes mixture
8. 8
   ろ過the precipitate was filtered off
9. 9
   その他to give pure product in 46% yield

実験手順

To a solution of (3aR,7aS)-tert-butyl 5-(3-aminopyridin-4-yl)-2-oxohexahydrooxazolo[4,5-c]pyridine-3(2H)-carboxylate (1.0 equiv.) in DMF (0.3 M) was added 3-amino-6-(2,6-difluorophenyl)picolinic acid (1.2 equiv.), EDC (1.2 equiv.) and HOAt (1.2 equiv.). The solution was stirred for 15 h. To the mixture was added water and the precipitate was filtered. To the filtrate was added EtOAc, and the organic solution was extracted (3 times), dried with Na2SO4, and concentrated to give an orange syrup. The crude was triturated with EtOAc and hexanes mixture and the precipitate was filtered off to give pure product in 46% yield. LCMS (m/z): 567.0 (MH+), LC Rt=3.03 min.

出典