Sodium Hydroxide → 2-carboxy-phenylacetic acid N-butyl-N-[2'-(1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-amide

HRID 2380683

Reaktionsgleichung

Reaktionsgleichung von HRID 2380683
[CH2:1]([N:5]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]#[N:32])=[CH:21][CH:20]=1)[C:6](=[O:17])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]([OH:16])=[O:15])[CH2:2][CH2:3][CH3:4].C([Sn]([N:46]=[N+:47]=[N-:48])(CCCC)CCCC)CCC.[OH-].[Na+].C(Cl)Cl.CO>C1(C)C(C)=CC=CC=1>[CH2:1]([N:5]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]2[NH:48][N:47]=[N:46][N:32]=2)=[CH:23][CH:24]=1)[C:6](=[O:17])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]([OH:16])=[O:15])[CH2:2][CH2:3][CH3:4]

Komponenten

6

Edukt 4

HCID 14798Sodium HydroxideHCID 4984872Tributyltin azideHCID 21226129Dichloromethane methanolHCID 539424252-carboxy-phenylacetic acid N-butyl-N-(2'-cyanobiphenyl-4-ylmethyl)-amide

Produkt 1

HCID 1784489242-carboxy-phenylacetic acid N-butyl-N-[2'-(1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

A solution of 2.50 g of 2-carboxy-phenylacetic acid N-butyl-N-(2'-cyanobiphenyl-4-ylmethyl)-amide and 6.50 g of tributyltin azide in 50 ml of xylene is heated under reflux for 15 hours. When cool, the mixture is stirred with 50 ml of 2N sodium hydroxide solution at room temperature for 30 minutes. The aqueous phase is acidified and extracted three times with 50 ml of CH2C2 each time. After customary treatment, the combined dichloromethane phases yield a crude product that, after chromatography on silica gel 60 (40-63 μm) using CH2Cl2 /CH3OH (97:3)) as eluant, yields 2-carboxy-phenylacetic acid N-butyl-N-[2'-(1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-amide that has an Rf value of 0.37 [CH2Cl2 /CH3OH (4:1)]. ##STR11##

Aufarbeitung

  1. temperatureunder reflux for 15 hours
  2. temperatureWhen cool
  3. extractionextracted three times with 50 ml of CH2C2 each time
  4. customAfter customary treatment, the combined dichloromethane phases yield a crude product that

Quellen und Nachweise

ORD-Eintrag
ord-f5648ef2d9994a0ba933532ae6e55815
Quelldatensatz
uspto-grants-1994_11
Patentnummer
US05369110

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