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

HRID 32856

반응식

HRID 32856 반응식
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

참가 물질

5

반응물 2

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

생성물 1

HCID 101561513-Maleimido-n-(3-triethoxysilanylpropyl)-propionamide수율 118.8%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2a0ac6f6b78746b28e6c2c019c15e97d
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07427678B2

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