Benzyl chloroformate → Benzyl (S)-2-(6-hydroxy-1H-indazol-1-yl)-1-methylethylcarbamate

HRID 1247005

Reaktionsgleichung

Reaktionsgleichung von HRID 1247005
[NH2:1][C@@H:2]([CH3:14])[CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:13])[CH:11]=2)[CH:6]=[N:5]1.C(=O)(O)[O-].[Na+].Cl[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22]>C1COCC1>[CH2:24]([O:23][C:21](=[O:22])[NH:1][C@@H:2]([CH3:14])[CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:13])[CH:11]=2)[CH:6]=[N:5]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Komponenten

5

Edukt 3

HCID 10387Benzyl chloroformateHCID 516892Sodium Bicarbonate2×HCID 135453290AL-34662

Produkt 1

HCID 135487328Benzyl (S)-2-(6-hydroxy-1H-indazol-1-yl)-1-methylethylcarbamateAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1-((S)-2-Aminopropyl)-1H-indazol-6-ol [prepared in accordance with commonly owned WO 02/098862A1, the contents of which are by this reference incorporated herein] (2.00 g, 10.5 mmol) was suspended in THF (20 mL) and saturated aqueous sodium bicarbonate (10 mL) and benzyl chloroformate (1.50 mL, 15 mol) were added. The mixture was stirred at room temperature until the starting amine dissolved. Saturated aqueous sodium bicarbonate (150 mL) was added and the reaction mixture extracted with ethyl acetate (3×150 mL). The combined organic layers were dried (magnesium sulfate), filtered, and evaporated to give a tan foam (2.65 g, 78%) which was pure by LC/MS (+APCI) m/z 326 (M+H+).

Aufarbeitung

  1. dissolutiondissolved
  2. extractionthe reaction mixture extracted with ethyl acetate (3×150 mL)
  3. dry with materialThe combined organic layers were dried (magnesium sulfate)
  4. filtrationfiltered
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-b0c0d8205a8f41f98ec32ad4ca9de451
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07129257B1

Verknüpfte Notizen

Wird geladen…