Di(succinimido) carbonate → HCID 178523862, Verbindung

HRID 230378

Reaktionsgleichung

Reaktionsgleichung von HRID 230378
[NH2:1][C@@H:2]([C:13]1[NH:14][CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:17]=1)[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[CH2:24]1[C:29](=[O:30])[N:28]([O:31][C:32](ON2C(=O)CCC2=O)=[O:33])[C:26](=[O:27])[CH2:25]1>C(#N)C>[O:27]=[C:26]1[CH2:25][CH2:24][C:29](=[O:30])[N:28]1[O:31][C:32]([NH:1][C@@H:2]([C:13]1[NH:14][CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:17]=1)[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1)=[O:33]

Komponenten

4

Edukt 2

HCID 676246Di(succinimido) carbonateHCID 178511782HCID 178511782, Verbindung

Produkt 1

HCID 178523862HCID 178523862, VerbindungAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

302.4 mg (1 mmol) of 2-{(1R)-1-amino-2-[indol-3-yl]ethyl}-4-phenyl-1H-imidazole previously dissolved in 20 mL of anhydrous acetonitrile was added dropwise to a solution of N,N′-disuccinimidylcarbonate (528 mg, 2 mmol, DSC) in 20 mL of anhydrous acetonitrile during 1.5 hour. After a further 4 hours of stirring at room temperature, the solvent was evaporated in vacuo and the residue redissolved in 30 mL of chloroform. Excess DSC was then discarded and the organic layer washed with water (4×30 mL), dried over MgSO4 and concentrated to obtain a brown solid (215 mg, 49%). 1H-NMR (CDCl3, 100 MHz) δ: 8.22 (brs, 1H); 8.1-7.08 (m, 12H); 5.9 (br s, 1H); 4.97 (dd, J=3.6 and 9.3 Hz, 1H); 3.75 (dd, J=3.6 and 14.8 Hz, 1H), 3.06 (dd, J=9.7 and 14.6 Hz, 1H); 2.96 (s, 2H); 2.89 (s, 2H). LC/MS: m/z=329 ((M+H)−SuOH.

Aufarbeitung

  1. customthe solvent was evaporated in vacuo
  2. dissolutionthe residue redissolved in 30 mL of chloroform
  3. washthe organic layer washed with water (4×30 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-055cded82b564de7b376687e76545765
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07566734B2

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