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Tetrahydrofuran → 3-[1,1-Dimethyl-2-(2,2-dimethyl-3-nitroxypropanoylamino)-ethylamino]-1-(3-methylbenzimidazol-4-yloxy)-propan-2-ol fumarate

HRID 1607126
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1607126
[CH3:1][C:2]([CH3:11])([CH2:6][O:7][N+:8]([O-:10])=[O:9])[C:3](Cl)=[O:4].O1CCCC1.[NH2:17][CH2:18][C:19]([NH:22][CH2:23][CH:24]([OH:37])[CH2:25][O:26][C:27]1[C:35]2[N:34]([CH3:36])[CH:33]=[N:32][C:31]=2[CH:30]=[CH:29][CH:28]=1)([CH3:21])[CH3:20].[C:38]([OH:45])(=[O:44])/[CH:39]=[CH:40]/[C:41]([OH:43])=[O:42]>CC(C)=O.C(Cl)Cl>[C:38]([OH:45])(=[O:44])/[CH:39]=[CH:40]/[C:41]([OH:43])=[O:42].[CH3:21][C:19]([NH:22][CH2:23][CH:24]([OH:37])[CH2:25][O:26][C:27]1[C:35]2[N:34]([CH3:36])[CH:33]=[N:32][C:31]=2[CH:30]=[CH:29][CH:28]=1)([CH3:20])[CH2:18][NH:17][C:3](=[O:4])[C:2]([CH3:11])([CH3:1])[CH2:6][O:7][N+:8]([O-:10])=[O:9]
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Komponenten

7

Edukt 4

HCID 8028Tetrahydrofuran2×HCID 444972Fumaric AcidHCID 198529363-(2-Amino-1,1-dimethylethylamino)-1-(3-methylbenzimidazol-4-yloxy)-propan-2-olHCID 200955153-Chloro-2,2-dimethyl-3-oxopropyl nitrate

Produkt 1

HCID 137153783-[1,1-Dimethyl-2-(2,2-dimethyl-3-nitroxypropanoylamino)-ethylamino]-1-(3-methylbenzimidazol-4-yloxy)-propan-2-ol fumarate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 1.4 g. 2,2-dimethyl-3-nitroxypropanoyl chloride in 50 ml. dry tetrahydrofuran is added dropwise at ambient temperature to a solution of 2.3 g. 3-(2-amino-1,1-dimethylethylamino)-1-(3-methylbenzimidazol-4-yloxy)-propan-2-ol in 150 ml. dry tetrahydrofuran, followed by further stirring for 2 hours. The reaction mixture is evaporated and chromatographed on silica gel with methylene chloride/methanol (4:2 v/v). The product obtained (2.0 g.) is dissolved in 60 ml. methylene chloride and mixed with 0.54 g. fumaric acid in 100 ml. acetone. The precipitate which separates out after the addition of 200 ml. diethyl ether is filtered off with suction and dried. There are obtained 2.3 g. (53% of theory) of the desired product in the form of crystals; m.p. 187°-190° C.

Aufarbeitung

  1. customThe reaction mixture is evaporated
  2. customchromatographed on silica gel with methylene chloride/methanol (4:2 v/v)
  3. customThe product obtained (2.0 g.)
  4. dissolutionis dissolved in 60 ml
  5. additionafter the addition of 200 ml
  6. filtrationdiethyl ether is filtered off with suction
  7. customdried
  8. customThere are obtained 2.3 g

Quellen und Nachweise

ORD-Eintrag
ord-ae3506e273154b26af140435f0456d58
Quelldatensatz
uspto-grants-1989_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04863949

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