Azido(trimethyl)stannane → 1-(1-Ethyl-propyl)-2-thiophen-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid [(S)-3-methyl-1-(1H-tetrazol-5-ylmethyl)-butyl]-amide

HRID 1750174Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1750174
[C:1]([CH2:3][C@@H:4]([NH:9][C:10]([C:12]1[CH:31]=[CH:30][C:15]2[N:16]([CH:25]([CH2:28][CH3:29])[CH2:26][CH3:27])[C:17]([CH2:19][C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)=[N:18][C:14]=2[CH:13]=1)=[O:11])[CH2:5][CH:6]([CH3:8])[CH3:7])#[N:2].[N:32]([Sn](C)(C)C)=[N+:33]=[N-:34]>C1(C)C=CC=CC=1.C(=O)(O)[O-].[Na+]>[CH3:7][CH:6]([CH3:8])[CH2:5][C@H:4]([NH:9][C:10]([C:12]1[CH:31]=[CH:30][C:15]2[N:16]([CH:25]([CH2:28][CH3:29])[CH2:26][CH3:27])[C:17]([CH2:19][C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)=[N:18][C:14]=2[CH:13]=1)=[O:11])[CH2:3][C:1]1[NH:34][N:33]=[N:32][N:2]=1

Komponenten

5

Edukt 2

HCID 5104973Azido(trimethyl)stannaneHCID 867143851-(1-Ethyl-propyl)-2-thiophen-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid ((S)-1-cyanomethyl-3-methyl-butyl)-amide

Produkt 1

HCID 1784460871-(1-Ethyl-propyl)-2-thiophen-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid [(S)-3-methyl-1-(1H-tetrazol-5-ylmethyl)-butyl]-amideAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

218 mg of 1-(1-ethyl-propyl)-2-thiophen-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid ((S)-1-cyanomethyl-3-methyl-butyl)-amide and 124 mg of azidotrimethyltin in 10 ml of dry toluene were heated under Argon for 48 h. The precipitated crude product was isolated by suction and then dissolved in 10% aqueous sodium bicarbonate solution and filtered with addition of charcoal. The pH of the filtrated was adjusted to 5, and the precipitated product was isolated by suction, washed with water and dried in vacuo to obtain 100 mg (42%) of 1-(1-Ethyl-propyl)-2-thiophen-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid [(S)-3-methyl-1-(1H-tetrazol-5-ylmethyl)-butyl]-amide.

Aufarbeitung

  1. customThe precipitated crude product
  2. customwas isolated by suction
  3. filtrationfiltered with addition of charcoal
  4. customthe precipitated product was isolated by suction
  5. washwashed with water
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4dad43cd23a74f7fa590439de06c5be4
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156796B2

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