Reaction #11952

Reaction equation

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

Solvents

methanol

Conditions

Workup

1. 1
   OtherAfter the reaction for 1 hour
2. 2
   Concentrationthe reaction solution was concentrated
3. 3
   Otherdried 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
   Concentrationthe reaction solution was concentrated
7. 7
   Otherdried 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
    OtherAfter the reaction for 1 hour
11. 11
    Concentrationthe reaction solution was concentrated
12. 12
    OtherThe residue was purified by silica gel column chromatography (4 g, chloroform/methanol/water=7/3/0.5)

Procedure

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.

Source