Reaktion #61134

Reaktionsgleichung

3-Maleimidopropionic acid N-hydroxysuccinimide ester

3-aminopropyltriethoxysilane

→

maleimide silane

Ausbeute 118.8%

3-maleimido-N-(3-triethoxysilanylpropyl)-propionamide

Ausbeute 118.8%

Lösungsmittel

CH2Cl2

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAn aliquot (0.15 mL) was removed by syringe
2. 2
   Einengenconcentrated in vacuo
3. 3
   EinengenThe reaction mixture was then concentrated in vacuo at 50-55° C.
4. 4
   Sonstigethe residue obtained
5. 5
   Waschenwashed with water (3×50 mL) and brine (50 mL)
6. 6
   Filtrationfiltered through granular Na2SO4
7. 7
   Einengenconcentrated under reduced pressure in vacuo

Vorschrift

3-Maleimidopropionic acid N-hydroxysuccinimide ester (18) (4.0 g, 15.03 mmol, 1.0 equiv.) was dissolved in N,N-dimethylformamide (75 mL) and 3-aminopropyltriethoxysilane (17) (5.06 mL, 15.03 mmol, 1 equiv.) was added and the reaction mixture was allowed to stir for 22 hours. An aliquot (0.15 mL) was removed by syringe, concentrated in vacuo, and the resulting oil was analyzed by 1H NMR spectroscopy. The oil was consistent with desired product. The reaction mixture was then concentrated in vacuo at 50-55° C. and the residue obtained was dissolved in CH2Cl2 (75 mL), washed with water (3×50 mL) and brine (50 mL), filtered through granular Na2SO4, and concentrated under reduced pressure in vacuo to provide 6.65 g (>100% due to residual N,N-dimethylformamide) of the crude maleimide-silane (19) as a light yellow oil. Crude (19) was used without purification. 1H NMR (300 MHz, CDCl3) δ 6.65 (s, 2H), 6.00 (s, 1H), 3.77 (q, J=7 Hz, 6H), 3.70 (m, 2H), 3.17 (m, 2H), 2.46 (m, 2H), 1.56 (m, 2H), 1.18 (t, J=7 Hz, 9H), 0.57 (m, 2H). 13C NMR (75 MHz, CDCl3) δ 170.36, 169.28, 134.09, 58.35, 41.77, 34.56, 34.21, 23.20, 18.20, 7.65. FB-MS (pos): [M+H]+ 373 (373.2 calcd).

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