Maleimide → HCID 44475354, compound

HRID 537641Notes

Reaction equation

HRID 537641 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[CH2:15](O)[CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH2:33][C:34]#[CH:35].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:56]1(=[O:62])[NH:60][C:59](=[O:61])[CH:58]=[CH:57]1>C1COCC1>[CH2:15]([N:60]1[C:56](=[O:62])[CH:57]=[CH:58][C:59]1=[O:61])[CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH2:33][C:34]#[CH:35]

Participants

6

Reactant 4

HCID 10935MaleimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 44475517HCID 44475517, compound

Product 1

HCID 44475354HCID 44475354, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropyl azodicarboxylate (730 μL, 3.43 mmol) was added dropwise into the ice cooled solution of 3,6,9,12,15,18-hexaoxahenicos-20-yn-1-ol 1 (1000 mg, 3.12 mmol), triphenylphosphine (900 mg, 3.43 mmol) and maleimide (456 mg, 4.70 mmol) in anhydrous THF (20 mL) under nitrogen atmosphere (FIG. 3). The resulting brown solution was allowed to war to room temperature and stirred for 1 hour at room temperature. The solvent was evaporated at the reduced pressure and the crude product was purified on a SiO2 column using hexanes/ethylacetate gradient 0-100% to yield 650 mg of yellow oil which was subsequently purified on semipreparative HPLC (System E) to provide 2 free of triphenylphosphine oxide as colorless oil 310 mg (25%). 1H NMR (400 MHz, CDCl3): δ 2.43 (t, J=2.36 Hz, 1H), 3.60-3.72 (m, 24H), 4.20 (d, J=2.37 Hz, 2H), 6.70 (s, 2H); 13C NMR (100.6 MHz, CDCl3): δ 37.2, 58.4, 67.8, 69.1, 70.1, 70.4-70.6, 74.5, 79.7, 134.1, 170.6; MS ESI (m/z): [M+H]+, calcd. for C19H30NO8, 400.19. found 400.0

Workup

  1. customwas allowed to war to room temperature
  2. customThe solvent was evaporated at the reduced pressure
  3. customthe crude product was purified on a SiO2 column

Sources & evidence

ORD record
ord-d64301a480d1498ebc7a4c322620f04a
Source dataset
uspto-grants-2014_10
Patent number
US08865122B2

Reaction notes

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