Tetrahydrofuran → Olmutinib

HRID 526057Notizen

Reaktionsgleichung

[NH2:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][CH:31]=1)[O:5][C:6]1[C:7]2[S:28][CH:27]=[CH:26][C:8]=2[N:9]=[C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)[N:11]=1.C([O-])(O)=O.[Na+].[O:37]1C[CH2:40][CH2:39][CH2:38]1.C(Cl)(=O)C=C>O>[CH3:25][N:22]1[CH2:21][CH2:20][N:19]([C:16]2[CH:15]=[CH:14][C:13]([NH:12][C:10]3[N:11]=[C:6]([O:5][C:4]4[CH:3]=[C:2]([NH:1][C:38](=[O:37])[CH:39]=[CH2:40])[CH:31]=[CH:30][CH:29]=4)[C:7]4[S:28][CH:27]=[CH:26][C:8]=4[N:9]=3)=[CH:18][CH:17]=2)[CH2:24][CH2:23]1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

The compound (3.69 mmol) obtained in Step 5 and NaHCO3 (11.07 mmol) were distilled with tetrahydrofuran (40 mL) and distilled water (6 mL), and acryloyl chloride (3.69 mmol) was added thereto slowly at 0° C. with stirring for 15 min. After the reaction was complete, the reaction mixture was distilled with dichloromethane and then washed with sat. NaHCO3 aqueous solution. The organic layer was dried with anhydrous sodium sulfate and then filtered and distilled under a reduced pressure, and the residue was separated by column chromatography (chloroform:methanol=20:1 (volume ratio)) to obtain the title compound (yield: 68.2%).

Aufarbeitung

additionwas added
distillationthe reaction mixture was distilled with dichloromethane
washwashed with sat. NaHCO3 aqueous solution
dry with materialThe organic layer was dried with anhydrous sodium sulfate
filtrationfiltered
distillationdistilled under a reduced pressure
customthe residue was separated by column chromatography (chloroform:methanol=20:1 (volume ratio))

Quellen und Nachweise

ORD-Eintrag: ord-6275d1204686462c934eb66da3a02f78
Quelldatensatz: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09345719B2

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