Carbon tetrabromide → HCID 178463279, Verbindung

HRID 1469159Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1469159
[C:1]([O:5][C:6]([N:8]([CH3:33])[C@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]([CH2:31][CH3:32])[C:16]2[C:17]([CH3:30])=[C:18]([CH:23]=[C:24]([C:26]#[C:27][CH2:28]O)[CH:25]=2)[C:19]([O:21][CH3:22])=[O:20])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Br)(Br)(Br)[Br:54]>C(Cl)Cl>[Br:54][CH2:28][C:27]#[C:26][C:24]1[CH:25]=[C:16]([N:15]([C@H:12]2[CH2:13][CH2:14][C@H:9]([N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH3:33])[CH2:10][CH2:11]2)[CH2:31][CH3:32])[C:17]([CH3:30])=[C:18]([CH:23]=1)[C:19]([O:21][CH3:22])=[O:20]

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 178463301HCID 178463301, Verbindung

Produkt 1

HCID 178463279HCID 178463279, VerbindungAusbeute 38,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of methyl 3-(((trans)-4-((tert-butoxycarbonyl)(methyl)amino)cyclohexyl)(ethyl)amino)-5-(3-hydroxyprop-1-yn-1-yl)-2-methylbenzoate (1.2 g, 2.62 mmol) in DCM (15 mL), PPh3 (1.37 g, 5.22 mmol) and CBr4 (1.7 g, 5.10 mmol) were added at 0° C. and reaction was stirred for 4 h 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 material was purified by column chromatography to afford the title compound (0.5 g, 38.5% yield).

Aufarbeitung

  1. customreaction
  2. customOn completion, reaction
  3. customwas quenched with ice water
  4. extractionextracted with dichloromethane
  5. washThe combined organic layers were washed with water
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe crude material was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-48379360e0984c2aa58f1b8a4d1723c3
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006242B2

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