Dimethylformamide → t-butyl [(1R)-2-(3-cyanophenoxy)-1-(4-iodobenzyl)ethyl]carbamate

HRID 747735Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 747735
[C:1]([C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:17][C@H:18]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([I:26])=[CH:22][CH:21]=1.CN(C)C=O>O>[C:1]([C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[O:9][CH2:17][C@H:18]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:19][C:20]1[CH:21]=[CH:22][C:23]([I:26])=[CH:24][CH:25]=1)#[N:2]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 133943-CyanophenolHCID 86760709t-butyl [(1R)-2-chloro-1-(4-iodobenzyl)ethyl]carbamate

Produkt 1

HCID 86760710t-butyl [(1R)-2-(3-cyanophenoxy)-1-(4-iodobenzyl)ethyl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

724 mg (6.08 mmol) of 3-cyanophenol and 1.12 g (8.1 mmol) of potassium carbonate were added to 1.6 g (0.60 mmol) of t-butyl [(1R)-2-chloro-1-(4-iodobenzyl)ethyl]carbamate and 25 ml of dimethylformamide, and they were stirred at 70° C. for 55 hours. The reaction liquid was diluted with water. After extraction with ethyl acetate, the organic layer was successively washed with water and saturated aqueous NaCl solution. The solvent was evaporated, and the residue was purified by the silica gel column chromatography to obtain the title compound.

Aufarbeitung

  1. customThe reaction liquid
  2. extractionAfter extraction with ethyl acetate
  3. washthe organic layer was successively washed with water and saturated aqueous NaCl solution
  4. customThe solvent was evaporated
  5. customthe residue was purified by the silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ead6881ae7e9418bbf9d9b7f2931aebd
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07396844B1

Notizen zur Reaktion

Wird geladen…