Hydrochloric Acid → [2-bromo-6-(tert-butoxycarbonyl)-3-cyclohexyl-1H-indol-1-yl]acetic acid

HRID 1714006Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1714006
[Br:1][C:2]1[N:3]([CH2:24][C:25]([O:27]C)=[O:26])[C:4]2[C:9]([C:10]=1[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[CH:8][CH:7]=[C:6]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:5]=2.Cl>O>[Br:1][C:2]1[N:3]([CH2:24][C:25]([OH:27])=[O:26])[C:4]2[C:9]([C:10]=1[CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1)=[CH:8][CH:7]=[C:6]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[CH:5]=2

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 68511006tert-butyl 2-bromo-3-cyclohexyl-1-(2-methoxy-2-oxoethyl)-1H-indole-6-carboxylate2×

Produkt 1

HCID 68509336[2-bromo-6-(tert-butoxycarbonyl)-3-cyclohexyl-1H-indol-1-yl]acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of LiOH monohydrate (4 eq) in H2O (0.05 M) was added to a solution of tert-butyl 2-bromo-3-cyclohexyl-1-(2-methoxy-2-oxoethyl)-1H-indole-6-carboxylate (1 eq) in a mixture THF: CH3OH (1:1) (from Step 6, 0.05 M). The reaction was heated at 50° C. for 2 h, before being allowed to cool to RT and reducing the volatiles in vacuo. The residue was then acidified with aqueous HCl (1 N) and the resultant precipitate filtered off, washed with water and dried in vacuo to afford the title compound (quant.); MS (ES+) m/z 436 (M+H)+, 438 (M+H)+.

Aufarbeitung

  1. temperatureto cool to RT
  2. filtrationthe resultant precipitate filtered off
  3. washwashed with water
  4. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0f60e1b48e2b4854be2ab0042fd394c8
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795247B2

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