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Pyridine → HCID 24750597, Verbindung

HRID 643696
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 643696
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([C:17]([CH3:22])([CH3:21])[C:18](O)=[O:19])(=[O:16])=[O:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:3][CH2:2]1.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.C(=O)(O)[O-].[NH4+].[N:48]1C=CC=CC=1>C(#N)C>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([C:17]([CH3:22])([CH3:21])[C:18]([NH2:48])=[O:19])(=[O:15])=[O:16])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:3][CH2:2]1
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Komponenten

6

Edukt 4

HCID 1049PyridineHCID 14013Ammonium BicarbonateHCID 90495Di-tert-butyl dicarbonateHCID 59253266HCID 59253266, Verbindung

Produkt 1

HCID 24750597HCID 24750597, VerbindungAusbeute 100.160,703 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel

Versuchsvorschrift

To a suspension of 2-{[1-(cyclopropylmethyl)-2-(2,2-dimethylpropyl)-1H-benzimidazol-5-yl]sulfonyl}-2-methylpropanoic acid (Step H, 200 mg, 0.51 mmol) and di-tert-butyl dicarbonate (145 mg, 0.66 mmol) in acetonitrile (3 mL) were added ammonium bicarbonate (48 mg, 0.61 mmol) and pyridine (48 mg, 0.61 mmol) at room temperature. The mixture was stirred at room temperature for 20 h and concentrated under reduced pressure. The residue was dissolved in water (30 mL) and dichloromethane (30 mL). The aqueous layer was separated and extracted with dichloromethane (30 mL). The combined organic layers were dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:3 as eluent) to afford the title compound (200 g, quant.) as a white solid.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in water (30 mL)
  3. customThe aqueous layer was separated
  4. extractionextracted with dichloromethane (30 mL)
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:3 as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-d0c0c58a94ec48a19b85caf4a639b68f
Quelldatensatz
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07700618B2

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