Water → HCID 68451363, Verbindung

HRID 511866Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 511866
[OH:1][C:2]1[CH:3]=[C:4]([C@H:8]2[CH2:10][C@@H:9]2[C:11]([NH:13][C@@H:14]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]([F:27])([F:26])[F:25])=[CH:18][N:17]=2)[CH3:15])=[O:12])[CH:5]=[CH:6][CH:7]=1.Cl[CH2:29][C:30]1([CH3:34])[CH2:33][O:32][CH2:31]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:29][C:30]1([CH2:34][O:1][C:2]2[CH:3]=[C:4]([C@H:8]3[CH2:10][C@@H:9]3[C:11]([NH:13][C@@H:14]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]([F:27])([F:25])[F:26])=[CH:18][N:17]=3)[CH3:15])=[O:12])[CH:5]=[CH:6][CH:7]=2)[CH2:33][O:32][CH2:31]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 791123-(Chloromethyl)-3-methyloxetaneHCID 68452925HCID 68452925, Verbindung

Produkt 1

HCID 68451363HCID 68451363, VerbindungAusbeute 49,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of (1S*,2S*)-2-(3-hydroxyphenyl)-N-((R)-1-(5-(2,2,2-trifluoroethoxy)pyridin-2-yl)ethyl)cyclopropanecarboxamide (15 mg, 0.039 mmol), 3-(Chloromethyl)-3-methyloxetane (24 mg, 0.197 mmol) and potassium carbonate (27 mg, 0.197 mmol) in DMF (2 mL) was heated at 70° C. with stirring for 15 hours. The mixture was poured into water, and the aqueous layer was extracted with ethyl acetate, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by preparative LC-MS to give 8.9 mg (49% yield) of the title compound.

Aufarbeitung

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by preparative LC-MS

Quellen und Nachweise

ORD-Eintrag
ord-00f3c2c4fd11444fb0c9af51e0fb26e6
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09101616B2

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