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3-Amino-1-propanol → (4-Fluoro-phenyl)-(3-hydroxy-propylamino)-acetic acid methyl ester

HRID 1644814
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1644814
[CH3:1][O:2][C:3](=[O:13])[CH:4](Br)[C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].[NH2:20][CH2:21][CH2:22][CH2:23][OH:24]>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:13])[CH:4]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)[NH:20][CH2:21][CH2:22][CH2:23][OH:24]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 90863-Amino-1-propanolHCID 11430Potassium CarbonateHCID 12717580Methyl 2-bromo-2-(4-fluorophenyl)acetate

Produkt 1

HCID 66773976(4-Fluoro-phenyl)-(3-hydroxy-propylamino)-acetic acid methyl esterAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

To a solution of bromo-(4-fluoro-phenyl)-acetic acid methyl ester (16.0 g) in chloroform (100 mL) was added potassium carbonate (17.9 g, finely ground) followed by 3-amino-1-propanol (4.87 g). The reaction was heated to 45° C. for 18 hours. The reaction was filtered and the filtrate was diluted with water and the phases were separated. The aqueous phase was further extracted with chloroform (3×25 mL) and the combined organics were washed with brine. The chloroform phase was dried over sodium sulfate, filtered and evaporated in vacuo to give the desired (4-fluoro-phenyl)-(3-hydroxy-propylamino)-acetic acid methyl ester (14.85 g, MS (ES+): 242.2 (MH+)) as a yellow oil which was used in the next step without further purification.

Aufarbeitung

  1. filtrationThe reaction was filtered
  2. additionthe filtrate was diluted with water
  3. customthe phases were separated
  4. extractionThe aqueous phase was further extracted with chloroform (3×25 mL)
  5. washthe combined organics were washed with brine
  6. dry with materialThe chloroform phase was dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-40afdde3d9d34abb9f55f3d86697f01a
Quelldatensatz
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08124636B2

Notizen zur Reaktion

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