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Lithium Hydroxide → (+/-)-3-(4-Ethylpyridin-2-yl)-4-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)butanoic Acid

HRID 2099755
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2099755
[CH2:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH:9]([CH2:16][C:17]2[CH:25]=[C:24]([CH3:26])[C:23]3[C:19](=[CH:20][N:21]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[N:22]=3)[CH:18]=2)[CH2:10][C:11]([O:13]CC)=[O:12])[CH:4]=1)[CH3:2].[OH-].[Li+]>O1CCCC1>[CH2:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH:9]([CH2:16][C:17]2[CH:25]=[C:24]([CH3:26])[C:23]3[C:19](=[CH:20][N:21]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:32])([CH3:34])[CH3:33])[N:22]=3)[CH:18]=2)[CH2:10][C:11]([OH:13])=[O:12])[CH:4]=1)[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 57794570(+/-)-Ethyl 3-(4-ethylpyridin-2-yl)-4-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)butanoate

Produkt 1

HCID 57794674(+/-)-3-(4-Ethylpyridin-2-yl)-4-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)butanoic Acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a flask containing (±)-ethyl 3-(4-ethylpyridin-2-yl)-4-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)butanoate (80 mg, 0.166 mmol, 1.0 equiv) in tetrahydrofuran (4 mL) was added lithium hydroxide (2.0 M, 0.34 mL, 4.0 equiv). The suspension was heated at 60° C. under nitrogen overnight. The reaction mixture was concentrated in vacuo. Hydrochloric acid (1 N, 0.6 mL) was added and the solution was extracted with ethyl acetate. The aqueous solution was adjusted to pH 7 with sodium hydroxide (1 N) and re-extracted with ethyl acetate. The combined ethyl acetate layers were washed with brine, dried over sodium sulfate and concentrated in vacuo to give a light yellow oil. MS (ESI) 454 (MH)+.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionHydrochloric acid (1 N, 0.6 mL) was added
  3. extractionthe solution was extracted with ethyl acetate
  4. extractionre-extracted with ethyl acetate
  5. washThe combined ethyl acetate layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto give a light yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-744c724ff79648e6b2ec58ce1045cd6a
Quelldatensatz
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07569578B2

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