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1-Propanol → Tanogitran

HRID 1593205
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1593205
Cl.[C:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH2:12][C:13]2[N:17]([CH3:18])[C:16]3[CH:19]=[CH:20][C:21]([C@@:23]([NH:32][CH2:33][C:34]([O:36]CCC)=[O:35])([C:25]([N:27]4[CH2:31][CH2:30][CH2:29][CH2:28]4)=[O:26])[CH3:24])=[CH:22][C:15]=3[N:14]=2)=[CH:7][CH:6]=1)(=[NH:4])[NH2:3].C(O)CC.[OH-].[Na+].Cl[Si](C)(C)C>CO.CS(C)=O>[C:2]([C:5]1[CH:6]=[CH:7][C:8]([NH:11][CH2:12][C:13]2[N:17]([CH3:18])[C:16]3[CH:19]=[CH:20][C:21]([C@@:23]([NH:32][CH2:33][C:34]([OH:36])=[O:35])([C:25]([N:27]4[CH2:31][CH2:30][CH2:29][CH2:28]4)=[O:26])[CH3:24])=[CH:22][C:15]=3[N:14]=2)=[CH:9][CH:10]=1)(=[NH:3])[NH2:4]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 10311-PropanolHCID 6397ChlorotrimethylsilaneHCID 14798Sodium HydroxideHCID 69248790HCID 69248790, Verbindung

Produkt 1

HCID 9826322Tanogitran

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl Sulfoxide
Lösungsmittel
HCID 887MethanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To a solution of 93.9 g (0.15 mol) of (R)-2-(4-amidinophenylaminomethyl)-1-methyl-5-[1-(n-propyloxycarbonylmethylamino)-1-(pyrrolidinocarbonyl)-ethyl]-benzimidazole-hydrochloride×1 equivalent n-propanol in 470 mL methanol are added 13.3 g (0.33 mol) of solid sodium hydroxide and this mixture is refluxed for 1.5 hours under an inert gas atmosphere. It is allowed to cool to 50° C. and within 10 minutes 22.8 mL (0.18 mmol) of chlorotrimethylsilan are added dropwise thereto. The mixture is diluted with 470 mL of dimethylsulphoxide and 370 mL of methanol are distilled off at 300 mbar/80° C. To eliminate sodium chloride the suspension is filtered hot. The filtrate is cooled to 20° C. and stirred for 3 hours at 20° C. The suspension formed is suction filtered and the filter cake is washed with 50 mL dimethylsulphoxide and 100 mL acetone. The filter cake is dried at 50° C. in the circulating air drier. The title compound is obtained as a colourless solid.

Aufarbeitung

  1. temperaturethis mixture is refluxed for 1.5 hours under an inert gas atmosphere
  2. additionare added dropwise
  3. distillationare distilled off at 300 mbar/80° C
  4. filtrationis filtered hot
  5. customThe suspension formed
  6. filtrationfiltered
  7. washthe filter cake is washed with 50 mL dimethylsulphoxide and 100 mL acetone
  8. customThe filter cake is dried at 50° C. in the circulating air drier

Quellen und Nachweise

ORD-Eintrag
ord-99446fe6442245b8a2bc69797339b739
Quelldatensatz
uspto-grants-2007_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07294721B2

Notizen zur Reaktion

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