Hydrochloric Acid → 2-{3-Chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenoxy}-pyrimidine-5-carboxylic acid

HRID 1095940Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1095940
C[O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]([CH3:32])[C:19]([C:25]3[CH:30]=[CH:29][N:28]=[C:27]([Cl:31])[CH:26]=3)([OH:24])[C:20]([F:23])([F:22])[F:21])=[C:14]([Cl:33])[CH:13]=2)=[N:9][CH:10]=1)=[O:4].[Li+].[OH-].Cl>C1COCC1.CO>[Cl:33][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][C:15]=1[CH:18]([CH3:32])[C:19]([C:25]1[CH:30]=[CH:29][N:28]=[C:27]([Cl:31])[CH:26]=1)([OH:24])[C:20]([F:23])([F:21])[F:22])[O:11][C:8]1[N:7]=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:10][N:9]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 595086402-{3-Chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenoxy}-pyrimidine-5-carboxylic acid methyl ester

Produkt 1

HCID 595087562-{3-Chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenoxy}-pyrimidine-5-carboxylic acidAusbeute 8,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815MeOH tetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2-{3-Chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenoxy}-pyrimidine-5-carboxylic acid methyl ester (27 mg) was dissolved in THF/methanol=5/1 (2.5 mL). The reaction mixture was cooled to 0° C. and aqueous LiOH solution (1.0 M, 0.092 mL) was added. The mixture was stirred at 0° C. for 1 hour. The reaction mixture was poured into ice/water and acidified with 1M aqueous HCl to pH 1. The aqueous phase was then extracted two times with ethyl acetate and the organic layers were washed with brine, dried over Na2SO4 and evaporated. The residue was purified by flash chromatography (silica gel, ethyl acetate:heptane=50:50 to 100:0) to give the title compound as a colorless amorphous foam (2.2 mg, 8.4%). MS (neg. ion, m/e)=486.4 [(M−H)−].

Aufarbeitung

  1. extractionThe aqueous phase was then extracted two times with ethyl acetate
  2. washthe organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe residue was purified by flash chromatography (silica gel, ethyl acetate:heptane=50:50 to 100:0)

Quellen und Nachweise

ORD-Eintrag
ord-c878d0cb61774f19b182a1d828859223
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138189B2

Notizen zur Reaktion

Wird geladen…