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Diethyl Ether → 2-(4-(2-(Phenylmethyloxycarbonylamino)ethyl)phenoxy)-2-methylbutanoic Acid

HRID 381261
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 381261
[C:1]1([CH2:7][O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(Cl)Cl.[OH-:25].[Na+].[CH3:27][CH2:28]OCC.C[C:33](=[O:36])[CH2:34][CH3:35]>>[C:1]1([CH2:7][O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][C:34]([CH3:35])([CH2:27][CH3:28])[C:33]([OH:36])=[O:25])=[CH:18][CH:19]=2)=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 5

HCID 3283Diethyl EtherHCID 6212ChloroformHCID 6569Methyl Ethyl Ketone2×HCID 14798Sodium HydroxideHCID 14103856benzyl N-(2-(4-hydroxyphenyl)ethyl)carbamate

Produkt 1

HCID 186694352-(4-(2-(Phenylmethyloxycarbonylamino)ethyl)phenoxy)-2-methylbutanoic Acid

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

A solution of 4-(2-(phenylmethyloxycarbonylamino)ethyl)phenol (5.74 g; 21.16 mmole) in 2-butanone (17 mL) and chloroform (6 g) was added dropwise to a mixture of sodium hydroxide (9.0 g; 225 mmole) and 2-butanone (67 mL) whilst keeping the reaction temperature below 30° C. The mixture was allowed to stir at 30° C. for 4 h. Ether (100 mL) was added and the resultant solid was collected by filtration and washed with ether (100 mL). The solid was dissolved in water (70 mL) and any residual ether removed by evaporation. 1N Hydrochloric acid was added to adjust the pH to 1, and the resulting oil was extracted with dichloromethane (3×50 mL). The combined extracts were dried (Na2SO4) and evaporated to afford a yellow oil (3.82 g; 49%).

Aufarbeitung

  1. customthe reaction temperature below 30° C
  2. filtrationthe resultant solid was collected by filtration
  3. washwashed with ether (100 mL)
  4. dissolutionThe solid was dissolved in water (70 mL)
  5. customany residual ether removed by evaporation
  6. addition1N Hydrochloric acid was added
  7. extractionthe resulting oil was extracted with dichloromethane (3×50 mL)
  8. dry with materialThe combined extracts were dried (Na2SO4)
  9. customevaporated
  10. customto afford a yellow oil (3.82 g; 49%)

Quellen und Nachweise

ORD-Eintrag
ord-3bfcf676f4b64c148044f07c3983f654
Quelldatensatz
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06306854B1

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