Reaktion #700398

Reaktionsgleichung

N-hydroxysuccinimide

N9 -(t-butoxycarbonyl)-N6,N9 -bis(2-methyl-2-triphenylmethylthiopropyl)-6,9-diazanonanoic acid

tris(2-aminoethyl)amine

diisopropylcarbodiimide

→

N9 -(t-butoxycarbonyl)-N6,N9 -bis(2-methyl-2-triphenylmethylthiopropyl)-6,9-diazanonanamide

Lösungsmittel

methylene chloride

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeBAT-BM was prepared
2. 2
   Sonstigeequipped with magnetic stir bar
3. 3
   Sonstigewithin 1 h
4. 4
   workup.STIRRINGstirring continued overnight
5. 5
   EinengenThe reaction mixture was then concentrated under reduced pressure
6. 6
   Sonstigethe residue partitioned between ethylacetate (150 mL) and 0.5M potassium carbonate (K2CO3 ; 150 mL)
7. 7
   SonstigeThe organic layer was separated
8. 8
   Waschenwashed with brine
9. 9
   Einengenconcentrated

Vorschrift

BAT-BM was prepared as follows. BAT acid (N9 -(t-butoxycarbonyl)-N6,N9 -bis(2-methyl-2-triphenylmethylthiopropyl)-6,9-diazanonanoic acid) (10.03 g, 10.89 mmol) and 75 mL of dry methylene chloride (CH2Cl2) were added to a 250 mL round-bottomed flask equipped with magnetic stir bar and argon balloon. To this solution was added diisopropylcarbodiimide (3.40 mL, 21.7 mmol, 199 mole %), followed by N-hydroxysuccinimide (3.12g, 27.1 mmol, 249 mole %). This solution was observed to become cloudy within 1 h, and was further incubated with stirring for a total of 4 h at room temperature. A solution of tris(2-aminoethyl)amine (30 mL, 200 mmol, 1840 mole %) in 30 mL methylene chloride was then added and stirring continued overnight. The reaction mixture was then concentrated under reduced pressure, and the residue partitioned between ethylacetate (150 mL) and 0.5M potassium carbonate (K2CO3 ; 150 mL). The organic layer was separated, washed with brine and concentrated to give the crude product N-[2-N',N'-bis(2-aminoethyl)aminoethyl)]-N9 -(t-butoxycarbonyl)-N6,N9 -bis(2-methyl-2-triphenylmethylthiopropyl)-6,9-diazanonanamide as a foam/oil.

Quelle