Phenacyl bromide → HCID 19939496, Verbindung

Reaktionsgleichung

[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].[CH2:48](Br)[C:49]([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)=[O:50]>>[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]([CH2:48][C:49]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)=[O:50])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Komponenten

Edukt 2

HCID 6259Phenacyl bromide

HCID 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 19939496HCID 19939496, VerbindungAusbeute 81 %

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 phenacyl bromide was carried out as described in Example 3, Step A, except that only 3 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 0.5-2.0% MeOH/CH2Cl2) to give the desired compound as a white foam in 81% yield, homogeneous by TLC in 2% MeOH/CH2Cl2, mass spectrum (FAB) 736 (M+1)+.

Aufarbeitung

customchromatographed over silica gel (25 mL for 0.162 mmole, gradient elution using 0.5-2.0% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag: ord-62290e99971941118e3b239557ca18f1
Quelldatensatz: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05411980

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