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Lithium hydroxide, monohydrate → (R)-2-Hydroxy-3-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)propanoic acid

HRID 501934
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 501934
C([O:4][C@H:5]([CH2:10][C:11]1[CH:19]=[C:18]([CH3:20])[C:17]2[C:13](=[CH:14][N:15]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[N:16]=2)[CH:12]=1)[C:6]([O:8]C)=[O:7])(=O)C.O.[OH-].[Li+]>O1CCCC1.CO.O>[OH:4][C@H:5]([CH2:10][C:11]1[CH:19]=[C:18]([CH3:20])[C:17]2[C:13](=[CH:14][N:15]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:27])([CH3:26])[CH3:28])[N:16]=2)[CH:12]=1)[C:6]([OH:8])=[O:7]
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Komponenten

6

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 59424274(R)-Methyl 2-acetoxy-3-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)propanoate

Produkt 1

HCID 59424393(R)-2-Hydroxy-3-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)propanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962
Water
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of (R)-methyl 2-acetoxy-3-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)propanoate (700 mg, 1.72 mmol) in tetrahydrofuran (6 mL) and methanol (6 mL) at 0° C. was added a solution of lithium hydroxide monohydrate (289 mg, 6.89 mmol) in water (6 mL). The reaction was stirred at 0° C. for 1 h. The reaction was concentrated, dissolved in 5 mL of water, cooled to 0° C., and treated with 1M hydrochloric acid until mildly acidic. A non-solid ppt formed. The suspension was extracted with ethyl acetate (2×), which were washed with brine, dried over magnesium sulfate, and concentrated to give 620 mg (quant.) which was pure by LC/MS and was used without purification. Mass spec.: 351.13 (MH)+.

Aufarbeitung

  1. concentrationThe reaction was concentrated
  2. dissolutiondissolved in 5 mL of water
  3. temperaturecooled to 0° C.
  4. additiontreated with 1M hydrochloric acid until mildly acidic
  5. customA non-solid ppt formed
  6. extractionThe suspension was extracted with ethyl acetate (2×), which
  7. washwere washed with brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated
  10. customto give 620 mg (quant.) which
  11. customwas used without purification

Quellen und Nachweise

ORD-Eintrag
ord-9af57409fd2c41488c07c1472465fa28
Quelldatensatz
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07772244B2

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