Ethyl bromoacetate → (4-tert-Butoxycarbonylamino-naphthalen-1-yloxy)-acetic Acid Ethyl Ester

HRID 1726961Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1726961
[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([OH:18])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]>CC(C)=O>[CH2:31]([O:30][C:28](=[O:29])[CH2:27][O:18][C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:19])=[CH:9][CH:10]=1)[CH3:32]

Komponenten

5

Edukt 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 10923237tert-Butyl (4-hydroxynaphthalen-1-yl)carbamate

Produkt 1

HCID 69037445(4-tert-Butoxycarbonylamino-naphthalen-1-yloxy)-acetic Acid Ethyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

3.33 g (12.8 mmol) of 4-hydroxy-naphthalen-1-yl-carbamic acid tert-butyl ester was dissolved in 60 ml of acetone and treated at 0° C. subsequently with 4.60 g (1.1 eq.) of cesium carbonate, 0.107 g (0.05 eq.) of KI, and 1.42 ml (1.0 eq.) of ethyl bromoacetate. After vigorous stirring for 1 h at ambient temperature, the solvent was evaporated and the residue redissolved in AcOEt. Washing with water, drying over magnesium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=75/25), yielded 4.28 g of the title product as off-white crystals.

Aufarbeitung

  1. customthe solvent was evaporated
  2. dissolutionthe residue redissolved in AcOEt
  3. washWashing with water
  4. dry with materialdrying over magnesium sulfate, and evaporation of the solvents

Quellen und Nachweise

ORD-Eintrag
ord-403b5e2d0f9c4a02984296bbf404cf8e
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07495001B2

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