Methanol → HCID 59852584, Verbindung

HRID 2373857Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2373857
CSC.[Cl:4][C:5]1[CH:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C@@H:19]([NH:23][C:24]([C:26]3[CH:27]=[C:28]([C:34]4[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][CH:35]=4)[CH:29]=[CH:30][C:31]=3[O:32]C)=[O:25])[CH2:20][O:21][CH3:22])=[CH:14][CH:13]=2)[CH:8]=[CH:9][C:10]=1[F:11].CO>C(Cl)Cl>[Cl:4][C:5]1[CH:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C@@H:19]([NH:23][C:24]([C:26]3[CH:27]=[C:28]([C:34]4[CH:35]=[CH:36][C:37]([C:40]([F:43])([F:41])[F:42])=[CH:38][CH:39]=4)[CH:29]=[CH:30][C:31]=3[OH:32])=[O:25])[CH2:20][O:21][CH3:22])=[CH:14][CH:13]=2)[CH:8]=[CH:9][C:10]=1[F:11]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 1068Dimethyl SulfideHCID 57717668HCID 57717668, Verbindung

Produkt 1

HCID 59852584HCID 59852584, VerbindungAusbeute 62,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

DMS (13 mg, 0.04 mmol) was added to a solution of 4-Methoxy-4′-trifluoromethyl-biphenyl-3-carboxylic acid [2-(3′-chloro-4′-fluoro-biphenyl-4-yl)-1-(R)-methoxymethyl-ethyl]-amide (24 mg, 0.04 mmol) in 3 mL of anhydrous CH2Cl2, at −78° C. and slowly allowed to come to room temperature and stirred for 2 h. After completion of the reaction, reaction was cooled to −78° C. and 0.5 mL of MeOH was added, solvent was removed under vacuum and the residue was taken in ethyl acetate (4 mL) and washed with aq NaHCO3 solution, water, brine and dried over Na2SO4. Solvent was removed under vacuum and silica gel column chromatography (Ethyl acetate: Hexanes) gave pure 4-Hydroxy-4′-trifluoromethyl-biphenyl-3-carboxylic acid [2-(3′-chloro-4′-fluoro-biphenyl-4-yl)-1-(R)-methoxymethyl-ethyl]-amide (14 mg).

Aufarbeitung

  1. customto come to room temperature
  2. customAfter completion of the reaction, reaction
  3. customsolvent was removed under vacuum
  4. washwashed with aq NaHCO3 solution, water, brine
  5. dry with materialdried over Na2SO4
  6. customSolvent was removed under vacuum and silica gel column chromatography (Ethyl acetate: Hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-f75d625773e145a4ab1fbabef51aa422
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07459472B2

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