Water → (S)-2-((7-bromo-4-(hydroxymethyl)-1H-indazol-5-yl)methyl)succinic acid

HRID 132455Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 132455
[Br:1][C:2]1[C:10]2[NH:9][N:8]=[CH:7][C:6]=2[C:5]2[CH2:11][O:12][C:13](=[O:21])[C@H:14]([CH2:16][C:17]([O:19]C)=[O:18])[CH2:15][C:4]=2[CH:3]=1.[OH2:22].O.[OH-].[Li+]>O1CCCC1.CO>[Br:1][C:2]1[CH:3]=[C:4]([CH2:15][C@@H:14]([CH2:16][C:17]([OH:19])=[O:18])[C:13]([OH:12])=[O:21])[C:5]([CH2:11][OH:22])=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2

Komponenten

6

Edukt 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrate2×HCID 59732087(S)-methyl 2-(4-bromo-8-oxo-6,7,8,10-tetrahydro-3H-oxepino[3,4-e]indazol-7-yl)acetate

Produkt 1

HCID 59732086(S)-2-((7-bromo-4-(hydroxymethyl)-1H-indazol-5-yl)methyl)succinic acidAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(S)-Methyl 2-(4-bromo-8-oxo-6,7,8,10-tetrahydro-3H-oxepino[3,4-e]indazol-7-yl)acetate (135 mg, 0.368 mmol) was dissolved in a mixture of tetrahydrofuran (4.0 mL) and methanol (4.0 mL). Water (4.0 mL) was added to the mixture followed by lithium hydroxide hydrate (31.5 mg, 0.751 mmol). Reaction stirred at room temperature for 5 hours. Another 30 mg of lithium hydroxide hydrate was added to the mixture. Reaction stirred at room temperature for 18 hours. Reaction was quenched with 1.6 mL 1N hydrochloric acid. Organic solvents were removed from the mixture by roto-vap. Material was extracted from the remaining aqueous twice with ethyl acetate and the aqueous phase was discarded. Organics were dried MgSO4, filtered and then concentrated to dryness. Title compound was obtained as white solid in 73% yield. MS (M−H)−=355.2, 357.1.

Aufarbeitung

  1. customReaction
  2. customReaction
  3. stirringstirred at room temperature for 18 hours
  4. customReaction
  5. customwas quenched with 1.6 mL 1N hydrochloric acid
  6. customOrganic solvents were removed from the mixture by roto-vap
  7. extractionMaterial was extracted from the remaining aqueous twice with ethyl acetate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-861e42cad64a40a5ba91fbb649fd6c36
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384931B2

Notizen zur Reaktion

Wird geladen…