HCID 68468290, Verbindung → Methyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3-fluorophenyl)acetate

HRID 453512Notizen

Reaktionsgleichung

[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:29]=[CH:28][C:14]([O:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:18][C:17]=3[F:27])=[C:13](N)[CH:12]=2)=[O:10])=[CH:4][CH:3]=1>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:29]=[CH:28][C:14]([O:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:18][C:17]=3[F:27])=[CH:13][CH:12]=2)=[O:10])=[CH:31][CH:32]=1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

Isobutyl nitrile (0.060 ml, 0.51 mmol) was diluted with DMF (2 mL), placed under nitrogen and heated to 60° C. followed by the addition of methyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)-2-aminophenoxy)-3-fluorophenyl)acetate (93 mg, 0.20 mmol) in 500 μL of DMF. The reaction was stirred 30 minutes and then cooled. The reaction was diluted with ethyl acetate and washed with 2N HCl and saturated sodium bicarbonate. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated. The material was purified by silica gel chromatography, eluting with hexanes:ethyl acetate (2:1) to yield methyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3-fluorophenyl)acetate (35 mg, 39% yield).

Aufarbeitung

temperaturecooled
washwashed with 2N HCl and saturated sodium bicarbonate
customThe layers were separated
dry with materialthe organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe material was purified by silica gel chromatography
washeluting with hexanes:ethyl acetate (2:1)

Quellen und Nachweise

ORD-Eintrag: ord-84ab1457d8ed423b82b507fc3ba5f6f1
Quelldatensatz: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08492437B2

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