Lithium Hydroxide → 2-[2-(Benzhydrylidene-amino)-3-fluoropyridin-4-ylmethyl]-3-oxobutanoic acid ethyl ester

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Reaktionsgleichung

[C:1](=[N:14][C:15]1[C:20]([F:21])=[C:19]([CH2:22]O)[CH:18]=[CH:17][N:16]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(Cl)(=O)=O.CC(C)([O-])C.[Li+].[CH2:35]([O:37][C:38](=[O:43])[CH2:39][C:40]([CH3:42])=[O:41])[CH3:36].[Na+].[I-].[Li+].[OH-]>C1COCC1.C(OCC)(=O)C>[CH2:35]([O:37][C:38](=[O:43])[CH:39]([CH2:22][C:19]1[CH:18]=[CH:17][N:16]=[C:15]([N:14]=[C:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:20]=1[F:21])[C:40](=[O:41])[CH3:42])[CH3:36]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

A mixture of [2-(benzhydrylidene-amino)-3-fluoropyridin-4-yl]-methanol (compound 8c-4) (5 g, 16.3 mmol), methanesulfonyl chloride (1.52 mL, 19.6 mmol) and lithium tert-butoxide (in THF) (18 mL, 18 mmol) in THF (40 mL) was stirred at 0° C. for 1 hour. The mixture was added to a solution of acetoacetic acid ethyl ester (4.16 mL, 32.7 mmol), lithium tert-butoxide (in THF) (19.6 mL, 19.6 mmol) and NaI (2.5 g, 16.3 mmol) in THF (18 mL). The solution was stirred at 50° C. for 3 hours, 0.2N LiOH (in water) and ethyl acetate were added thereto, and the solution was washed with 0.2N LiOH (in water) and saturated saline. After drying over anhydrous magnesium sulfate, the solvent was distilled away under reduced pressure to yield the title compound (6.98 g, quant.).

Aufarbeitung

stirringThe solution was stirred at 50° C. for 3 hours
washthe solution was washed with 0.2N LiOH (in water) and saturated saline
dry with materialAfter drying over anhydrous magnesium sulfate
distillationthe solvent was distilled away under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-0671f1612ea54dcf91d2a4f6416a9c46
Quelldatensatz: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08278465B2

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