Reaktion #48765

Reaktionsgleichung

2-aminothiazole

HATU

3-((1S)-2-{[tert-Butyl(dimethyl)silyl]oxy}-1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]benzoic acid

→

title compound

Ausbeute 70.0%

3-((1S)-2-{[tert-Butyl(dimethyl)silyl]oxy}-1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]-N-1,3-thiazol-2-ylbenzamide

Ausbeute 70.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was evaporated
2. 2
   workup.DISSOLUTIONthe residue was dissolved in saturated aqueous sodium hydrogencarbonate (30 mL)
3. 3
   SonstigeThe organic layer was separated
4. 4
   Waschenwashed with saturated aqueous ammonium chloride (30 mL)
5. 5
   Trocknenthen dried (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated
8. 8
   SonstigePurification by column chromatography
9. 9
   Wascheneluting with 1:2 to 2:1 ethyl acetate

Vorschrift

HATU (513 mg, 1.35 mmol) was added to 3-((1S)-2-{[tert-Butyl(dimethyl)silyl]oxy}-1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]benzoic acid (520 mg, 1.08 mmol) followed by addition of DMF (5 mL), disopropylethylamine (0.48 mL) and 2-aminothiazole (135 mg, 1.35 mmol) and the reaction was stirred under argon for 4 h. The solvent was evaporated and the residue was dissolved in saturated aqueous sodium hydrogencarbonate (30 mL) and ethyl acetate (50 mL). The organic layer was separated, washed with saturated aqueous ammonium chloride (30 mL) then dried (MgSO4), filtered and evaporated. Purification by column chromatography, eluting with 1:2 to 2:1 ethyl acetate:hexanes, afforded the title compound as a colourless oil (425 mg, 70%).

Quelle