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4-Cyanobenzoic acid → N-[(1R)-2-(3-cyanophenoxy)-1-(4-iodobenzyl)ethyl]-4-cyanobenzamide

HRID 747736
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 747736
[C:1]([C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][CH:27]=1)[O:6][CH2:7][C@H:8]([NH:17][C:18](=[O:24])OC(C)(C)C)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([I:16])=[CH:12][CH:11]=1)#[N:2].[C:28]([C:30]1[CH:38]=[CH:37][C:33](C(O)=O)=[CH:32][CH:31]=1)#[N:29].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>Cl.O1CCOCC1.O1CCOCC1.O.C(N(CC)CC)C>[C:1]([C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][CH:27]=1)[O:6][CH2:7][C@H:8]([NH:17][C:18](=[O:24])[C:33]1[CH:37]=[CH:38][C:30]([C:28]#[N:29])=[CH:31][CH:32]=1)[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([I:16])=[CH:14][CH:15]=1)#[N:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 120874-Cyanobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86760710t-butyl [(1R)-2-(3-cyanophenoxy)-1-(4-iodobenzyl)ethyl]carbamate

Produkt 1

HCID 68831582N-[(1R)-2-(3-cyanophenoxy)-1-(4-iodobenzyl)ethyl]-4-cyanobenzamide

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 312751,4-DioxaneLösungsmittelHCID 204431481,4-Dioxane hydrochlorideLösungsmittel

Versuchsvorschrift

1.44 g (3.01 mmol) of t-butyl [(1R)-2-(3-cyanophenoxy)-1-(4-iodobenzyl)ethyl]carbamate was dissolved in 5 ml of 4 N dioxane hydrochloride and 2.5 ml of dioxane, and the solution was stirred for 15 hours. The solvent was evaporated under reduced pressure, and the residue was dissolved in 10 ml of dichloromethane. 488 mg (3.3 mmol) of 4-cyanobenzoic acid 1.3 ml (9.3 mmol) of triethylamine, 633 mg (1.5 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 445 mg (3.3 mmol) of 1-hydroxybenzotriazole were added to the solution, and they were stirred for 16 hours. The reaction liquid was diluted with water. After the extraction with ethyl acetate, the organic layer was successively washed with water, 1 N sodium hydroxide and saturated aqueous NaCl solution, and then dried over anhydrous magnesium sulfate. The solvent was evaporated. The residue was purified by the silica gel column chromatography to obtain the title compound.

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in 10 ml of dichloromethane
  3. customThe reaction liquid
  4. extractionAfter the extraction with ethyl acetate
  5. washthe organic layer was successively washed with water, 1 N sodium hydroxide and saturated aqueous NaCl solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. customThe residue was purified by the silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-74825b9d5ea34663a00c65a2a17597a7
Quelldatensatz
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07396844B1

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