Triethylamine → Methanesulfonic acid 3-chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-benzyl ester

HRID 333799Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 333799
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][C:3]=1[CH:10]([CH3:24])[C:11]([C:17]1[CH:22]=[CH:21][N:20]=[C:19]([Cl:23])[CH:18]=1)([OH:16])[C:12]([F:15])([F:14])[F:13].CCN(CC)CC.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>C1COCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[CH:10]([CH3:24])[C:11]([C:17]1[CH:22]=[CH:21][N:20]=[C:19]([Cl:23])[CH:18]=1)([OH:16])[C:12]([F:15])([F:14])[F:13])[CH2:8][O:9][S:33]([CH3:32])(=[O:35])=[O:34]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 252544493-(2-Chloro-4-hydroxymethyl-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-ol

Produkt 1

HCID 86629101Methanesulfonic acid 3-chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 3-(2-chloro-4-hydroxymethyl-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-ol (50 mg, Example 112) in THF (1 mL) was added NEt3 (30 mg, 0.03 mL) under argon at −10° C. Methanesulfonyl chloride (18 mg, 0.01 mL) was added and the mixture was allowed to stir for 30 minutes. The reaction mixture was diluted with ethyl acetate and washed successively with sat. KHCO3 solution and brine. The organic layer was dried over Na2SO4 and evaporated to give the desired compound as light yellow, viscous oil that was used without further purification (53 mg). MS (m/e)=358.1 (MH+).

Aufarbeitung

  1. washwashed successively with sat. KHCO3 solution and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-8833e721195043c89182c96d03c9ffb3
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883786B2

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