Sodium Hydroxide → 5-(5-(Tert-butoxycarbonyl)-2-methylphenyl)-2-(4-fluorophenyl)furo[2,3-b]pyridine-3-carboxylic acid

HRID 219412Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 219412
[OH-].[Na+].[C:3]([O:7][C:8]([C:10]1[CH:11]=[CH:12][C:13]([CH3:36])=[C:14]([C:16]2[CH:17]=[C:18]3[C:24]([C:25]([O:27]C)=[O:26])=[C:23]([C:29]4[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=4)[O:22][C:19]3=[N:20][CH:21]=2)[CH:15]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>CO.C1COCC1.CCOC(C)=O>[C:3]([O:7][C:8]([C:10]1[CH:11]=[CH:12][C:13]([CH3:36])=[C:14]([C:16]2[CH:17]=[C:18]3[C:24]([C:25]([OH:27])=[O:26])=[C:23]([C:29]4[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=4)[O:22][C:19]3=[N:20][CH:21]=2)[CH:15]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4]

Komponenten

6

Edukt 2

HCID 14798Sodium HydroxideHCID 67217142HCID 67217142, Verbindung

Produkt 1

HCID 674056235-(5-(Tert-butoxycarbonyl)-2-methylphenyl)-2-(4-fluorophenyl)furo[2,3-b]pyridine-3-carboxylic acidAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

NaOH (1.4 mL, 1.37 mmol) was added to a stirring solution of methyl 5-(5-(tert-butoxycarbonyl)-2-methylphenyl)-2-(4-fluorophenyl)furo[2,3-b]pyridine-3-carboxylate (211 mg, 0.457 mmol) in MeOH (2.3 mL) and THF (2.3 mL) at 60° C. It was allowed to stir for 4 hours. The mixture was diluted with EtOAc and washed with 1M HCl, and sat NaCl. The organic phase was dried over Na2SO4, filtered and concentrated to give the expected product 5-(5-(tert-butoxycarbonyl)-2-methylphenyl)-2-(4-fluorophenyl)furo[2,3-b]pyridine-3-carboxylic acid (205 mg, 0.457 mmol, quant.) consistent by LCMS crude which was used directly in the next step. LC-MS retention time: 1.88 min; m/z (MH+): 448. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Waters XBridge 5u C18 4.6×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 5 ml/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 3 min, a hold time of 1 min, and an analysis time of 4 min where solvent A was 5% MeOH/95% H2O/10 mM ammonium acetate and solvent B was 5% H2O/95% MeOH/10 mM ammonium acetate. MS data was determined using a Micromass Platform for LC in electrospray mode.

Aufarbeitung

  1. washwashed with 1M HCl
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-930ba1c1b7b0485fb20dc496698f03c4
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198449B2

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