Reaktion #166257

Reaktionsgleichung

7-(2-fluoro-4-methylsulfanyl-phenylamino)-benzo[d]isothiazole-6-carboxylic acid ((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-amide

hydrochloric acid

→

title compound

Ausbeute 26.8%

7-(2-Fluoro-4-methylsulfanyl-phenylamino)-benzo[d]isothiazole-6-carboxylic acid ((R)-2,3-dihydroxy-propoxy)-amide

Ausbeute 26.8%

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenbefore being concentrated in vacuo
2. 2
   Waschenwashed with a saturated aqueous solution of sodium hydrogen carbonate
3. 3
   Trocknendried (Na2SO4)
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporated in vacuo

Vorschrift

To a solution of 7-(2-fluoro-4-methylsulfanyl-phenylamino)-benzo[d]isothiazole-6-carboxylic acid ((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-amide (170 mg, 0.37 mmol) in MeOH (2 mL) was added a 1.0M aqueous solution of hydrochloric acid (0.80 mL). The reaction mixture was stirred at room temperature for 1 hour before being concentrated in vacuo. The residue was taken up in ethyl acetate, washed with a saturated aqueous solution of sodium hydrogen carbonate followed by brine, dried (Na2SO4), filtered and evaporated in vacuo. The resultant residue was subjected to flash chromatography (Si—PPC, gradient 0% to 100%, MeOH in DCM) to afford the title compound as a yellow solid (42 mg, 26%). LCMS (Method A): RT=8.80 min, [M+H]+=478. 1H NMR (CD3OD) 8.81 (1 H, s), 7.63-7.56 (2 H, m), 7.12-7.04 (3 H, m), 4.10-4.04 (1 H, m), 3.98-3.86 (2 H, m), 3.64-3.55 (2 H, m), 2.50 (3 H, s).

Quelle