Methanol, magnesium salt (2:1) → (S)-dimethyl 2-((3,7-dichloro-4-(hydroxymethyl)-1H-indazol-5-yl)methyl)succinate

HRID 2378925Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2378925
C([O:4][CH2:5][C:6]1[C:14]([CH2:15][C@@H:16]([CH2:22][C:23]([O:25][CH2:26]C)=[O:24])[C:17]([O:19][CH2:20]C)=[O:18])=[CH:13][C:12]([Cl:28])=[C:11]2[C:7]=1[C:8]([Cl:29])=[N:9][NH:10]2)(=O)C.C[O-].[Mg+2].C[O-]>CO>[Cl:29][C:8]1[C:7]2[C:11](=[C:12]([Cl:28])[CH:13]=[C:14]([CH2:15][C@@H:16]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[C:17]([O:19][CH3:20])=[O:18])[C:6]=2[CH2:5][OH:4])[NH:10][N:9]=1

Komponenten

4

Edukt 2

HCID 164537Methanol, magnesium salt (2:1)HCID 178471822HCID 178471822, Verbindung

Produkt 1

HCID 178500726(S)-dimethyl 2-((3,7-dichloro-4-(hydroxymethyl)-1H-indazol-5-yl)methyl)succinateAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

(S)-Diethyl 2-((4-(acetoxymethyl)-3,7-dichloro-1H-indazol-5-yl)methyl)succinate (1.30 g, 2.92 mmol) was dissolved in methanol (45 mL). 6-10% Magnesium methoxide in methanol (8.4 mL, 6.35 mmol) was added to the mixture. Reaction stirred at room temperature for 16 hours. Reaction was quenched with 14 mL 1N hydrochloric acid. Methanol was removed from the mixture by roto-vap. Residue was treated with aqueous sodium bicarbonate. Material was extracted twice with ethyl acetate and the aqueous phase was discarded. The combined organic phases were washed with water and the aqueous phase was discarded. Organics were dried MgSO4, filtered and then concentrated to dryness. Title compound was obtained as dark amber oil in 91% yield. MS (M−H)−=373.0, 375.0.

Aufarbeitung

  1. customReaction
  2. customReaction
  3. customwas quenched with 14 mL 1N hydrochloric acid
  4. customMethanol was removed from the mixture by roto-vap
  5. additionResidue was treated with aqueous sodium bicarbonate
  6. extractionMaterial was extracted twice with ethyl acetate
  7. washThe combined organic phases were washed with water
  8. filtrationfiltered
  9. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-306bdca1d0bd40638464931dfc408001
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07470680B2

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