alpha,4-Dichloroanisole → 5-n-Butyl-2-(4-chlorophenoxymethyl)-2,4-dihydro-4-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]-3H-1,2,4-triazol-3-one

HRID 36220

Reaktionsgleichung

Reaktionsgleichung von HRID 36220
[CH2:1]([C:5]1[N:6]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]3[N:28]([C:29]([C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[N:27]=[N:26][N:25]=3)=[CH:14][CH:13]=2)[C:7](=[O:10])[NH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].Cl[CH2:49][O:50][C:51]1[CH:56]=[CH:55][C:54]([Cl:57])=[CH:53][CH:52]=1>>[CH2:1]([C:5]1[N:6]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]3[N:28]([C:29]([C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=4)([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)[C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)[N:27]=[N:26][N:25]=3)=[CH:16][CH:17]=2)[C:7](=[O:10])[N:8]([CH2:49][O:50][C:51]2[CH:56]=[CH:55][C:54]([Cl:57])=[CH:53][CH:52]=2)[N:9]=1)[CH2:2][CH2:3][CH3:4]

Komponenten

3

Edukt 2

HCID 88801alpha,4-DichloroanisoleHCID 199393865-n-Butyl-2,4-dihydro-4-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]-3H-1,2,4-triazol-3-one

Produkt 1

HCID 199395075-n-Butyl-2-(4-chlorophenoxymethyl)-2,4-dihydro-4-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]-3H-1,2,4-triazol-3-oneAusbeute 55 %

Versuchsvorschrift

The alkylation of 5-n-butyl-2,4-dihydro-4-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]-3H-1,2,4-triazol-3-one (from Example 2, Step D) with α,4-dichloroanisole was carried out as described in Example 3, Step A, except that only 5 equivalents of the alkylating agent was used. After work-up, the residue was flash chromatographed over silica gel (25 mL for 0.162 mmole, gradient elution using 0.25-1.0% MeOH/CH2Cl2) to give the desired material as a colorless oil in 55% yield, homogeneous by TLC in 2% MeOH/CH2Cl2, mass spectrum (FAB) 758 (M+1)+.

Aufarbeitung

  1. customchromatographed over silica gel (25 mL for 0.162 mmole, gradient elution using 0.25-1.0% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-e0e86bf8405e4202baa3105b58509213
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05411980

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