(3-Aminopropyl)triethoxysilane → 3-Maleimido-n-(3-triethoxysilanylpropyl)-propionamide

HRID 32856

反応式

HRID 32856 の反応式
C1C(=O)N(O[C:9]([CH2:11][CH2:12][N:13]2[C:18](=[O:19])[CH:17]=[CH:16][C:14]2=[O:15])=[O:10])C(=O)C1.[NH2:20][CH2:21][CH2:22][CH2:23][Si:24]([O:31][CH2:32][CH3:33])([O:28][CH2:29][CH3:30])[O:25][CH2:26][CH3:27]>CN(C)C=O.C(Cl)Cl>[C:14]1(=[O:15])[N:13]([CH2:12][CH2:11][C:9]([NH:20][CH2:21][CH2:22][CH2:23][Si:24]([O:31][CH2:32][CH3:33])([O:25][CH2:26][CH3:27])[O:28][CH2:29][CH3:30])=[O:10])[C:18](=[O:19])[CH:17]=[CH:16]1

参加物

5

反応物 2

HCID 13521(3-Aminopropyl)triethoxysilaneHCID 46205972,5-dioxopyrrolidin-1-yl 3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanoate

生成物 1

HCID 101561513-Maleimido-n-(3-triethoxysilanylpropyl)-propionamide収率 118.8%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  1. customAn aliquot (0.15 mL) was removed by syringe
  2. concentrationconcentrated in vacuo
  3. concentrationThe reaction mixture was then concentrated in vacuo at 50-55° C.
  4. customthe residue obtained
  5. washwashed with water (3×50 mL) and brine (50 mL)
  6. filtrationfiltered through granular Na2SO4
  7. concentrationconcentrated under reduced pressure in vacuo

出典と根拠

ORDレコード
ord-2a0ac6f6b78746b28e6c2c019c15e97d
出典データセット
uspto-grants-2008_09
特許番号
US07427678B2

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