Potassium Hydroxide → {3-[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-6-cyclopropylpyridin-3-yl]-4-methoxyphenyl}acetic acid

HRID 604674Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 604674
[F:1][C:2]([F:44])([F:43])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:25]([C:26]4[CH:27]=[C:28]([CH2:34][C:35]([O:37]C)=[O:36])[CH:29]=[CH:30][C:31]=4[O:32][CH3:33])=[CH:24][CH:23]=[C:22]([CH:39]4[CH2:41][CH2:40]4)[N:21]=3)[C@H:14]2[CH3:42])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[OH-].[K+]>CO>[F:44][C:2]([F:1])([F:43])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:25]([C:26]4[CH:27]=[C:28]([CH2:34][C:35]([OH:37])=[O:36])[CH:29]=[CH:30][C:31]=4[O:32][CH3:33])=[CH:24][CH:23]=[C:22]([CH:39]4[CH2:40][CH2:41]4)[N:21]=3)[C@H:14]2[CH3:42])[CH:6]=[C:7]([C:9]([F:11])([F:12])[F:10])[CH:8]=1

Komponenten

4

Edukt 2

HCID 14797Potassium HydroxideHCID 57576297methyl {3-[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-6-cyclopropylpyridin-3-yl]-4-methoxyphenyl}acetate

Produkt 1

HCID 24970135{3-[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-6-cyclopropylpyridin-3-yl]-4-methoxyphenyl}acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of methyl {3-[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-6-cyclopropylpyridin-3-yl]-4-methoxyphenyl}acetate (43 mg, 0.069 mmol) in MeOH (4 mL) was added 4M KOH (200 μL, 0.8 mmol). The reaction was stirred at room temperature for 4 hours and then quenched with HOAc (75 μL), diluted with EtOAc (30 μL), and washed with water and brine (10 mL each). The organic layer was dried (Na2SO4), filtered, and concentrated. Purification of the residue by flash chromatography on silica gel (0 to 100% EtOAc/hexanes) afforded {3-[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-6-cyclopropylpyridin-3-yl]-4-methoxyphenyl}acetic acid. LCMS=609.4 (M+H)+. 1H NMR (500 MHz, CDCl3): δ 7.84 (s, 1H), 7.72 (s, 2H), 7.39 (d, J=7.8 Hz, 1H), 7.27 (m, 1H), 7.14 (d, J=7.8 Hz, 1H), 7.07 (bs, 1H), 6.93 (d, J=8.5 Hz, 1H), 5.53 (bs, 1H), 4.85 (d, J=16.0 Hz, 1H), 3.86-4.20 (m, 2H), 3.78 (s, 3H), 3.61 (s, 2H), 2.07 (m, 1H), 1.00-1.10 (m, 4H), 0.54-0.70 (m, 3H).

Aufarbeitung

  1. customquenched with HOAc (75 μL)
  2. additiondiluted with EtOAc (30 μL)
  3. washwashed with water and brine (10 mL each)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the residue by flash chromatography on silica gel (0 to 100% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-10ea2d24a3434b6b9708f746fcc43b6c
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07910592B2

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