Hydrochloric Acid → HCID 178440077, Verbindung

HRID 52986

Reaktionsgleichung

Reaktionsgleichung von HRID 52986
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:19]([C:26]([OH:29])([CH3:28])[CH3:27])[N:18]=[C:17]2[CH2:30][CH2:31][CH3:32])=[CH:11][CH:10]=1)#[N:2].C([Sn]([N:46]=[N+:47]=[N-:48])(CCCC)CCCC)CCC.C(=O)([O-])O.[Na+].Cl>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[OH:29][C:26]([C:19]1[N:18]=[C:17]([CH2:30][CH2:31][CH3:32])[N:16]([CH2:15][C:12]2[CH:13]=[CH:14][C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[C:1]3[NH:48][N:47]=[N:46][N:2]=3)=[CH:10][CH:11]=2)[C:20]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22])([CH3:27])[CH3:28]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4984872Tributyltin azideHCID 15461993Ethyl 1-((2'-cyano(1,1'-biphenyl)-4-yl)methyl)-4-(1-hydroxy-1-methylethyl)-2-propyl-1H-imidazole-5-carboxylate

Produkt 1

HCID 178440077HCID 178440077, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 1.00 g of ethyl 1-(2'-cyanobiphenyl-4-yl)methyl-4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate [prepared as described in Example 71(b)] and 100 g of tributyltin azide in 7.5 ml of toluene was stirred at 100° C. for 5 days. 2.5 g of sodium hydrogencarbonate and 20 ml of water were then added to the mixture, and the resulting mixture was stirred at room temperature for 8 hours. At the end of this time, the mixture was diluted with ethyl acetate and acidified with 3N aqueous hydrochloric acid to a pH value of 3. The ethyl acetate layer was separated, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure, to give ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(tetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate as a syrup. 0.80 g of trityl chloride was added to a solution of the whole of this syrup in 15 ml of pyridine, and the mixture was stirred at 60° C. for 4 hours. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, and the residue was purified by column chromatography through silica gel, using a 1:1 by volume mixture of ethyl acetate and hexane as the eluent; it was then crystallized in diisopropyl ether, to give 1.15 g of the title compound as crystals.

Aufarbeitung

  1. customThe ethyl acetate layer was separated
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated by evaporation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-632fcdb4843d4784b5b8a7569b5ca0ed
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616599

Verknüpfte Notizen

Wird geladen…