Reaktion #325918

Reaktionsgleichung

(R)-3-(2-methylpropan-2-ylsulfinamido)-3,3-bis(3-(trifluoromethoxy)phenyl)propanamide

MeOH

→

3-(2-methylpropan-2-ylsulfinamido)-3,3-bis(3-(trifluoromethoxy)phenyl)-propanamide

Ausbeute 76.3%

Lösungsmittel

NH3

ethylene glycol

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeat 130° C. for 1200 sec under microwave irradiation
2. 2
   TemperaturAfter cooling
3. 3
   Sonstigethe cap was removed
4. 4
   workup.ADDITIONH2O was added
5. 5
   ExtraktionThe mixture was extracted with EtOAc (3×)
6. 6
   Waschenwashed with H2O and brine
7. 7
   Trocknendried over Na2SO4
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated
10. 10
    SonstigeThe residue was purified by flash chromatography (silica gel, hexanes/EtOAc

Vorschrift

(R)-3-(2-methylpropan-2-ylsulfinamido)-3,3-bis(3-(trifluoromethoxy)phenyl)propanamide (prepared as described for Procedure 11, 0.70 g, 1.33 mmol) was dissolved in 8N NH3 in ethylene glycol (6 mL) at room temperature in a microwave vial. The reaction mixture was heated at 120° C. for 1200 sec, and then at 130° C. for 1200 sec under microwave irradiation. After cooling, the cap was removed, and H2O was added. The mixture was extracted with EtOAc (3×), washed with H2O and brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (silica gel, hexanes/EtOAc, then 10% MeOH in EtOAc) to give 3-(2-methylpropan-2-ylsulfinamido)-3,3-bis(3-(trifluoromethoxy)phenyl)-propanamide as white solid (0.52 g, yield: 76%) LCMS: 3.88 min [M+1]513.28 (4 min gradient, MeOH/H2O 0.1% TFA); 1H NMR (400 MHz, CDCl3) δ ppm 7.40-7.29 (m, 3H), 7.22-7.12 (m, 3H), 7.11-7.02 (m, 2H), 6.29 (m, 2H), 5.40 (s, br, 1H), 3.78 (d, J=14.50 Hz, 1H), 3.71 (s, 2H), 3.35 (d, J=14.50 Hz, 1H), 1.21-1.28 (m, 9H).

Quelle