반응 #730339

반응 방정식

4-nitrophenyl chloroformate

methyl (R)-3-(4-benzyloxy-3,5-dimethyl-phenyl)-2-hydroxy-propionate

3-piperidin-4-yl-1H-quinoline-2-one

→

(R)-2-(4-benzyloxy-3,5-dimethyl-phenyl)-1-methoxycarbonyl-ethyl 4-(2-oxo-1,2-dihydro-quinolin-3-yl)-piperidine-1-carboxylate

용매

THF

pyridine

pyridine

반응 조건

후처리

1. 1
   workup.STIRRINGthe reaction mixture was stirred for 2 h at 60° C
2. 2
   workup.STIRRINGstirred for 4 h at 100° C
3. 3
   기타The reaction mixture was evaporated down i.vac
4. 4
   기타and the residue was purified by HPLC
5. 5
   workup.ADDITIONThe fractions containing the product
6. 6
   기타evaporated down i.vac
7. 7
   여과filtered
8. 8
   세척washed with 20 mL water
9. 9
   기타dried at 50° C.

실험 절차

Under a nitrogen atmosphere 0.91 g (4.38 mmol) 4-nitrophenyl chloroformate in 10 mL THF were metered into 20 mL pyridine within 10 min at a bath temperature of 60° C., the mixture was stirred for 10 min, then 1.38 g (4.38 mmol) methyl (R)-3-(4-benzyloxy-3,5-dimethyl-phenyl)-2-hydroxy-propionate in 40 mL pyridine were added and the reaction mixture was stirred for 2 h at 60° C. The reaction solution was combined with 1.00 g (4.38 mmol) 3-piperidin-4-yl-1H-quinoline-2-one and stirred for 4 h at 100° C. The reaction mixture was evaporated down i.vac. and the residue was purified by HPLC. The fractions containing the product were combined, evaporated down i.vac., the residue was made alkaline with 15% K2CO3 solution, the precipitate was suction filtered, washed with 20 mL water and dried at 50° C.

출처