Lithium Hydroxide → US9249085, I(am)

HRID 1771803Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1771803
[F:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[CH:6][C:5]([CH3:15])=[CH:4][C:3]=1[CH2:16][NH:17][C:18]1[C:19]([CH3:33])=[C:20]([CH:29]=[CH:30][C:31]=1[CH3:32])[O:21][CH2:22][C:23]([O:25]C(C)C)=[O:24].[Li+].[OH-]>C1COCC1>[F:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[CH:6][C:5]([CH3:15])=[CH:4][C:3]=1[CH2:16][NH:17][C:18]1[C:19]([CH3:33])=[C:20]([CH:29]=[CH:30][C:31]=1[CH3:32])[O:21][CH2:22][C:23]([OH:25])=[O:24]

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 89443725Isopropyl 2-[3-[[2-fluoro-3-(3-fluorophenyl)-5-methyl-phenyl]methylamino]-2,4-dimethyl-phenoxy]acetate

Produkt 1

HCID 89443873US9249085, I(am)Ausbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of isopropyl 2-[3-[[2-fluoro-3-(3-fluorophenyl)-5-methyl-phenyl]methylamino]-2,4-dimethyl-phenoxy]acetate (80 mg, 0.18 mmol, 1.0 eq) in THF (8 mL) at 0° C. was added LiOH (2M aqueous solution, 4 mL, 8.0 mmol). The reaction mixture was allowed to warm to room temperature and stirred overnight. The THF was removed and the remaining aqueous solution was diluted with water. The pH was adjusted to pH 4-6 by addition of diluted HCl. The solid precipitate that formed was collected by filtration, washed with water and dried in vacuo to give target compound as a yellow solid (30 mg, 41%).

Aufarbeitung

  1. customThe THF was removed
  2. additionthe remaining aqueous solution was diluted with water
  3. additionThe pH was adjusted to pH 4-6 by addition of diluted HCl
  4. customThe solid precipitate that formed
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-714660e684c04824925cf676593423d7
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09249085B2

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