Methyl iodide → HCID 178463214, Verbindung

HRID 1527790Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1527790
[Br:1][C:2]1[CH:3]=[C:4]([N:13]([C@H:16]2[CH2:21][CH2:20][C@H:19]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18][CH2:17]2)[CH2:14][CH3:15])[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[H-].[Na+].[CH3:32]I>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([N:13]([C@H:16]2[CH2:17][CH2:18][C@H:19]([N:22]([C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])[CH3:32])[CH2:20][CH2:21]2)[CH2:14][CH3:15])[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178463215HCID 178463215, Verbindung

Produkt 1

HCID 178463214HCID 178463214, VerbindungAusbeute 97,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of methyl 5-bromo-3-(((trans)-4-((tert-butoxycarbonyl)amino)cyclohexyl)(ethyl)amino)-2-methylbenzoate (3 g, 6.41 mmol, see, e.g., WO2012142504) in THF (30 mL), NaH (0.184 g, 7.69 mmol) was added at 0° C. and stirred it at same temperature for 20 min. Then methyl iodide (9.10 g, 64.10 mmol) was added at 0° C. and reaction was stirred for overnight at room temperature. On completion, reaction was quenched with ice water and extracted with dichloromethane. The combined organic layers were washed with water, dried, concentrated under reduced pressure. The crude compound was purified by column chromatography to afford the crude title compound that was used without further purification (3 g, 97.4% yield).

Aufarbeitung

  1. customreaction
  2. stirringwas stirred for overnight at room temperature
  3. customOn completion, reaction
  4. customwas quenched with ice water
  5. extractionextracted with dichloromethane
  6. washThe combined organic layers were washed with water
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customThe crude compound was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-93beedd14b284c41bf2e6672dadc357e
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09089575B2

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