Reaktion #597447

Reaktionsgleichung

(S)-2-(2-(3-(benzyloxy)phenyl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate

hydrogen

pyridine

Tf2O

→

product

Ausbeute 82.5%

(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-(trifluoromethylsulfonyloxy)phenyl)benzo[d]thiazol-6-yl)ethyl pivalate

Ausbeute 82.5%

Lösungsmittel

EtOH EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction was reacted at room temperature for 1 h
2. 2
   Sonstigethe catalyst was removed over Celite pad
3. 3
   Einengenthe solution was concentrated down to dryness
4. 4
   workup.DISSOLUTIONThe residue was dissolved in DCM (5 mL), to the solution
5. 5
   SonstigeThen the reaction was quenched by sat. NaHCO3
6. 6
   Extraktionextracted by DCM
7. 7
   Trocknendried over MgSO4
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated down
10. 10
    Sonstigepurified by silica gel column (0-40% EtOAc in hexanes)

Vorschrift

To a solution of (S)-2-(2-(3-(benzyloxy)phenyl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate (410 mg, 0.638 mmol) in EtOH/EtOAc (1:1, 4 mL) was added Pd/C (10%, 600 mg). Then hydrogen balloon was attached to the flask, and the reaction was reacted at room temperature for 1 h. After the reaction was finished, the catalyst was removed over Celite pad and the solution was concentrated down to dryness. The residue was dissolved in DCM (5 mL), to the solution was added pyridine (2 mL), Tf2O (210 μL, 1.25 mmol) at 0° C. and the reaction was stirred at 0° C. for 1 h. Then the reaction was quenched by sat. NaHCO3, extracted by DCM, dried over MgSO4, filtered, concentrated down and purified by silica gel column (0-40% EtOAc in hexanes) to give the product (360 mg, 82%). LCMS-ESI+: calc'd for C32H33ClF3NO6S2: 684.1 (M+H+); Found: 684.1 (M+H+).

Quelle