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

HRID 61830

Reaktionsgleichung

Reaktionsgleichung von HRID 61830
[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-ylmethoxy)-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-50247f053a544f818d766f3e22719b19
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440922B2

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