Hydrochloric Acid → 9-Bromo-3-chloro-8-((R)-2,3-dihydroxy-propoxy)-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-one

HRID 2275206

Reaktionsgleichung

Reaktionsgleichung von HRID 2275206
[Cl:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[C:7](=[O:31])[C:8]4[CH:20]=[C:19]([Br:21])[C:18]([O:22][CH2:23][C@H:24]5[CH2:28][O:27]C(C)(C)[O:25]5)=[CH:17][C:9]=4[C:10]([CH3:16])([CH3:15])[C:11]=3[NH:12]2)=[CH:4][CH:3]=1.Cl>CO>[Br:21][C:19]1[C:18]([O:22][CH2:23][C@H:24]([OH:25])[CH2:28][OH:27])=[CH:17][C:9]2[C:10]([CH3:15])([CH3:16])[C:11]3[NH:12][C:13]4[C:5]([C:6]=3[C:7](=[O:31])[C:8]=2[CH:20]=1)=[CH:4][CH:3]=[C:2]([Cl:1])[CH:14]=4

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 668343203-Chloro-9-bromo-8-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl methoxy)-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-one

Produkt 1

HCID 668343559-Bromo-3-chloro-8-((R)-2,3-dihydroxy-propoxy)-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-oneAusbeute 50,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

3-Chloro-9-bromo-8-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl methoxy)-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-one (Compound S7-1, 56 mg, 0.11 mmol) was dissolved in methanol (5 mL), added with 1 N hydrochloric acid (0.2 ml), and stirred at 50° C. for 2 hr. After cooling, the reaction solution was concentrated under reduced pressure and the resulting residues were added with methanol to obtain a precipitated solid, which was then filtered to obtain the title compound (white powder, 26 mg).

Aufarbeitung

  1. temperatureAfter cooling
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. additionthe resulting residues were added with methanol
  4. customto obtain a precipitated solid, which
  5. filtrationwas then filtered

Quellen und Nachweise

ORD-Eintrag
ord-a2685fe122e149a1b73a3fc5c14e1cb0
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09126931B2

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