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Hydrochloric Acid → Ethyl 4-[2-(2-tert-butoxycarbonylaminoethyl)-5-isopropylphenoxy]butyrate

HRID 733350
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 733350
[OH:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17].C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32].Cl>CN(C)C=O>[C:16]([O:15][C:14]([NH:13][CH2:12][CH2:11][C:3]1[CH:4]=[CH:5][C:6]([CH:8]([CH3:9])[CH3:10])=[CH:7][C:2]=1[O:1][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[O:20])([CH3:18])([CH3:17])[CH3:19]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 18457008tert-butyl N-[2-(2-hydroxy-4-isopropylphenyl)ethyl]carbamate

Produkt 1

HCID 17856236Ethyl 4-[2-(2-tert-butoxycarbonylaminoethyl)-5-isopropylphenoxy]butyrate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

tert-Butyl N-[2-(2-hydroxy-4-isopropylphenyl)ethyl]-carbamate (0.234 g) and 0.116 g of potassium carbonate were suspended in 5 mL of N,N-dimethylformamide. To the stirred suspension was added dropwise 0.126 mL of ethyl 4-bromobutyrate at room temperature, and the mixture was stirred at room temperature for 16 hours. To the reaction mixture were added 10 mL of 1 mol/L hydrochloric acid and then 20 mL of water, and the mixture was extracted with ethylacetate. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate-hexane) to give 0.283 g of ethyl 4-[2-(2-tert-butoxycarbonylaminoethyl)-5-isopropylphenoxy]-butyrate.

Aufarbeitung

  1. extraction20 mL of water, and the mixture was extracted with ethylacetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-fec258e250564ccc8dc5f07c27033c1f
Quelldatensatz
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07589126B2

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