반응 #819770

반응 방정식

pyridine-3,5-dicarboxylic acid

diisopropylethylamine

2-chlorotritylchloride resin

methylpropylamine

benzotriazole-1-yl-oxy-tris-pyrrolidinophosphonium hexafluorophosphate

→

title compound

수율 50.0%

5-(Methyl-propylcarbamoyl)-nicotinic acid

수율 50.0%

용매

dichloromethane

DMF

dichloromethane

반응 조건

후처리

1. 1
   workup.ADDITIONmix for 3 h
2. 2
   여과Filter
3. 3
   세척wash the resin
4. 4
   workup.ADDITIONwith a 17:2:1 mixture of dichloromethane
5. 5
   workup.ADDITIONmix for 1 h
6. 6
   여과Filter
7. 7
   세척wash the resin with dichloromethane (2×10 mL)
8. 8
   workup.ADDITIONAdd a solution of 5% trifluoroacetic acid in dichloromethane (10 mL) to the resin
9. 9
   여과Filter the resin
10. 10
    세척wash with dichloromethane (2×10 mL)
11. 11
    농축Combine the filtrates and concentrate

실험 절차

Add a solution of pyridine-3,5-dicarboxylic acid (220 mg, 1.32 mmol), diisopropylethylamine (918 μL, 5.28 mmol), and DMF (1.5 mL) in dichloromethane (10 mL) to 2-chlorotritylchloride resin (11.0 g, 1.1 mmol) in a peptide synthesis vessel and mix for 3 h. Filter and wash the resin with a 17:2:1 mixture of dichloromethane:methanol:diisopropylethylamine, followed by dichloromethane. Add a solution of methylpropylamine (225 μL, 2.2 mmol), and benzotriazole-1-yl-oxy-tris-pyrrolidinophosphonium hexafluorophosphate (1.14 g, 2.2 mmol) in dichloromethane (10 mL) to the resin and mix for 1 h. Filter and wash the resin with dichloromethane (2×10 mL). Add a solution of 5% trifluoroacetic acid in dichloromethane (10 mL) to the resin and let stand for 10 min. Filter the resin and wash with dichloromethane (2×10 mL). Combine the filtrates and concentrate to give the title compound (110 mg, 50%).

출처