Water → 5-(6,7-Bis(palmitoyloxy)-4-thiaheptanoyl)amino-2-(1,3-bis(t-butyloxycarbonyl)propyl)isoindolin-1-one

HRID 1720832Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1720832
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([CH:12]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:13][CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:5]2.[C:29]([O:46][CH:47]([CH2:55][O:56][C:57](=[O:73])[CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH3:72])[CH2:48][S:49][CH2:50][CH2:51][C:52](O)=[O:53])(=[O:45])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44].O>N1C=CC=CC=1.P(Cl)(Cl)Cl>[C:29]([O:46][CH:47]([CH2:55][O:56][C:57](=[O:73])[CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH3:72])[CH2:48][S:49][CH2:50][CH2:51][C:52]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([CH:12]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:13][CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:5]2)=[O:53])(=[O:45])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]

Komponenten

6

Edukt 3

HCID 962WaterHCID 105562786,7-Bis(palmitoyloxy)-4-thiaheptanoic acidHCID 224186435-Amino-2-(1,3-bis-(t-butyloxycarbonyl)propyl)isoindolin-1-one

Produkt 1

HCID 224185935-(6,7-Bis(palmitoyloxy)-4-thiaheptanoyl)amino-2-(1,3-bis(t-butyloxycarbonyl)propyl)isoindolin-1-oneAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 24387Phosphorus trichlorideLösungsmittel

Versuchsvorschrift

To a solution of 5-amino-2-(1,3-bis-(t-butyloxycarbonyl)propyl)isoindolin-1-one (178 mg) in pyridine (2.3 ml), phosphorus trichloride (0.020 ml) was added, followed by stirring at room temperature for 2 hours. To this mixture, 6,7-bis(palmitoyloxy)-4-thiaheptanoic acid (150 mg) was added, followed by stirring at room temperature for 24 hours. After addition of water, the reaction mixture was extracted with ethyl acetate. The extract was washed with a 5% aqueous solution of citric acid, a saturated aqueous solution of sodium hydrogen carbonate and saturated saline, and dried over anhydrous sodium sulfate, and the solvent was distilled off. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate =2:1) to yield the title compound (208 mg, yield 91%) as a wax-like substance.

Aufarbeitung

  1. stirringby stirring at room temperature for 24 hours
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe extract was washed with a 5% aqueous solution of citric acid
  4. dry with materiala saturated aqueous solution of sodium hydrogen carbonate and saturated saline, and dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off
  6. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate =2:1)

Quellen und Nachweise

ORD-Eintrag
ord-8c3d48d247374c6096723add277105c7
Quelldatensatz
uspto-grants-1996_04
Patentnummer
US05506267

Notizen zur Reaktion

Wird geladen…