Dimethylformamide → HCID 86638442, Verbindung

HRID 1009875Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1009875
CN(C)C=O.[CH2:6]([O:13][C@@H:14]1[C@@H:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@H:18]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@@H:17]([CH2:36][O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[O:16][C@H:15]1[C:45]1[CH:50]=[C:49]([CH2:51][C:52]2[CH:57]=[CH:56][C:55]([OH:58])=[CH:54][C:53]=2[CH3:59])[C:48]([CH3:60])=[CH:47][C:46]=1[O:61][CH2:62][C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Br[CH2:70][CH2:71][N:72]1[C:76](=[O:77])[C:75]2=[CH:78][CH:79]=[CH:80][CH:81]=[C:74]2[C:73]1=[O:82].C(=O)([O-])[O-].[K+].[K+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].O>[CH2:6]([O:13][C@@H:14]1[C@@H:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@H:18]([O:28][CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C@@H:17]([CH2:36][O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[O:16][C@H:15]1[C:45]1[CH:50]=[C:49]([CH2:51][C:52]2[CH:57]=[CH:56][C:55]([O:58][CH2:70][CH2:71][N:72]3[C:73](=[O:82])[C:74]4[C:75](=[CH:78][CH:79]=[CH:80][CH:81]=4)[C:76]3=[O:77])=[CH:54][C:53]=2[CH3:59])[C:48]([CH3:60])=[CH:47][C:46]=1[O:61][CH2:62][C:63]1[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 11430Potassium CarbonateHCID 67304108(1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-5-(4-hydroxy-2-methylbenzyl)-4-methylphenyl]-D-glucitol

Produkt 1

HCID 86638442HCID 86638442, VerbindungAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a N,N-dimethylformamide solution (5.0 mL) of (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-5-(4-hydroxy-2-methylbenzyl)-4-methylphenyl]-D-glucitol (340 mg, 0.40 mmol) and N-(2-bromoethyl)phthalimide (1.02 g, 4.0 mmol) were added potassium carbonate (553 mg, 4.0 mmol) and n-Bu4NI (14 mg, 0.038 mmol). The reaction mixture was stirred at 80° C. for 3.5 hours. After the mixture was cooled to room temperature, water was added thereto, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried with anhydrous magnesium sulfate. The drying agent was filtered off, and the solvent was evaporated under reduced pressure to obtain a residue. Thus obtained residue was purified with silica gel column chromatography (hexane:ethyl acetate=3:1) to obtain the title compound (60 mg, 15%) as a pale yellow oily compound.

Aufarbeitung

  1. temperatureAfter the mixture was cooled to room temperature
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationThe drying agent was filtered off
  6. customthe solvent was evaporated under reduced pressure
  7. customto obtain a residue
  8. customThus obtained residue was purified with silica gel column chromatography (hexane:ethyl acetate=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-5f875fb6dab8495dbcfe03cddd2d0e46
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973012B2

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