Phenol → Esomeprazole BINOL

HRID 453671

Reaktionsgleichung

Reaktionsgleichung von HRID 453671
[CH:1]1[CH:2]=[CH:3][C:4]2[C:10]([C:11]3[C:20]([OH:21])=[CH:19][CH:18]=[C:17]4[C:12]=3[CH:13]=[CH:14][CH:15]=[CH:16]4)=[C:9]([OH:22])[CH:8]=[CH:7][C:5]=2[CH:6]=1.C1(O)C=CC=CC=1.[CH3:30][C:31]1[CH:32]=[N:33][C:34]([CH2:40][S+:41]([O-:53])[C:42]2[NH:43][C:44]3[CH:45]=[CH:46][C:47]([O:51][CH3:52])=[CH:48][C:49]=3[N:50]=2)=[C:35]([CH3:39])[C:36]=1[O:37][CH3:38]>C1(C)C=CC=CC=1>[CH3:30][C:31]1[CH:32]=[N:33][C:34]([CH2:40][S+:41]([O-:53])[C:42]2[NH:43][C:44]3[CH:45]=[CH:46][C:47]([O:51][CH3:52])=[CH:48][C:49]=3[N:50]=2)=[C:35]([CH3:39])[C:36]=1[O:37][CH3:38].[CH:15]1[CH:14]=[CH:13][C:12]2[C:11]([C:10]3[C:9]([OH:22])=[CH:8][CH:7]=[C:5]4[C:4]=3[CH:3]=[CH:2][CH:1]=[CH:6]4)=[C:20]([OH:21])[CH:19]=[CH:18][C:17]=2[CH:16]=1

Komponenten

5

Edukt 3

HCID 996PhenolHCID 11762BinolHCID 178488147HCID 178488147, Verbindung

Produkt 1

HCID 178488158Esomeprazole BINOL

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

BINOL (4.14 g; 14.47 mmol) and phenol (1.36 g; 14.47 mmol) were added to toluene (100 ml) at 20-30° C. and heated the mixture to 45° C. Omeprazole (5 g; 14.47 mmol) was added to the mixture and stirred at 40-45° C. for 30 min. The solution was cooled to 20-30° C. and stirred for 2 h to crystallize the product. Hexane (50 ml) was added to the reaction mass and stirred for 15 h at 20-30° C. for complete crystallization of title compound, which was filtered, washed with toluene-hexane mixture and dried to obtain white solid of inclusion complex of esomeprazole-BINOL.

Aufarbeitung

  1. temperatureThe solution was cooled to 20-30° C.
  2. stirringstirred for 2 h
  3. customto crystallize the product
  4. additionHexane (50 ml) was added to the reaction mass
  5. stirringstirred for 15 h at 20-30° C. for complete crystallization of title compound, which
  6. filtrationwas filtered
  7. washwashed with toluene-hexane mixture
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-cb69ed2ebeb54603859f451540c283d3
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492551B2

Verknüpfte Notizen

Wird geladen…