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Water → US9249085, I(au)

HRID 1771837
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1771837
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][C:3]=1[CH2:15][NH:16][C:17]1[C:18]([F:32])=[C:19]([CH:28]=[CH:29][C:30]=1[F:31])[O:20][CH2:21][C:22]([O:24]C(C)C)=[O:23].[Li+].[OH-].O>C1COCC1>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][C:3]=1[CH2:15][NH:16][C:17]1[C:18]([F:32])=[C:19]([CH:28]=[CH:29][C:30]=1[F:31])[O:20][CH2:21][C:22]([OH:24])=[O:23]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 89444175Isopropyl 2-[3-[(2,3-dimethyl-5-phenyl-phenyl)methylamino]-2,4-difluoro-phenoxy]acetate

Produkt 1

HCID 89444124US9249085, I(au)Ausbeute 80,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of isopropyl 2-[3-[(2,3-dimethyl-5-phenyl-phenyl)methylamino]-2,4-difluoro-phenoxy]acetate (110 mg, 0.25 mmol, 1.0 eq) in THF (4 mL) was added LiOH (52 mg, 1.2 mmol, 5 eq) and water (3 mL) and the reaction mixture stirred at room temperature for 1 h. The THF was removed under reduced pressure and the remaining aqueous solution was adjusted to pH 4-5 by addition of 1M HCl. The mixture was extracted with EtOAc and the combined organic extracts washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo to give the title compound as a yellow oil (80 mg, 80%).

Aufarbeitung

  1. customThe THF was removed under reduced pressure
  2. additionthe remaining aqueous solution was adjusted to pH 4-5 by addition of 1M HCl
  3. extractionThe mixture was extracted with EtOAc
  4. washthe combined organic extracts washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5ede37b9ed2346f1b95693ed9e45e801
Quelldatensatz
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09249085B2

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