Реакция #11952

Уравнение реакции

compound

Nα-(4-(8-quinolylaminomethyl)benzoyl)-Nδ-Boc-L-ornithine

hydrochloric acid dioxane

→

title compound

(S)-2-(4-(8-quinolylaminomethyl)benzoylamino)-5-(2-picolylamino)valeric acid

Растворители

methanol

Условия реакции

Обработка

1. 1
   ДругоеAfter the reaction for 1 hour
2. 2
   Концентрированиеthe reaction solution was concentrated
3. 3
   Другоеdried under reduced pressure
4. 4
   workup.DISSOLUTIONThe resulting residue was dissolved in methanol (2 ml)
5. 5
   workup.ADDITIONpyridine-2-aldehyde (18 μl) and triethylamine (27 μl) were added
6. 6
   Концентрированиеthe reaction solution was concentrated
7. 7
   Другоеdried under reduced pressure
8. 8
   workup.DISSOLUTIONThe residue was again dissolved in methanol (2 ml)
9. 9
   workup.ADDITIONsodium borohydride (22 mg) was added
10. 10
    ДругоеAfter the reaction for 1 hour
11. 11
    Концентрированиеthe reaction solution was concentrated
12. 12
    ДругоеThe residue was purified by silica gel column chromatography (4 g, chloroform/methanol/water=7/3/0.5)

Методика

The compound obtained in Example 16-3 (122.6 mg) was dissolved in methanol (1.2 ml) and 4 mol/l hydrochloric acid/dioxane solution (1.2 ml) was added. After the reaction for 1 hour, the reaction solution was concentrated and dried under reduced pressure. The resulting residue was dissolved in methanol (2 ml), and pyridine-2-aldehyde (18 μl) and triethylamine (27 μl) were added. After 15 hours, the reaction solution was concentrated and dried under reduced pressure. The residue was again dissolved in methanol (2 ml) and sodium borohydride (22 mg) was added. After the reaction for 1 hour, the reaction solution was concentrated. The residue was purified by silica gel column chromatography (4 g, chloroform/methanol/water=7/3/0.5) to obtain the title compound (114.0 mg) as an orange solid.

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