Reaktion #60267

Reaktionsgleichung

sodium periodate

6-(4-bromo-2-methyl-phenylamino)-3-(4,5-dihydroxy-pentyl)-7-fluoro-3H-benzoimidazole-5-carboxylic acid cyclopropylmethoxy-amide

THF

phosphate

→

pure desired product

Ausbeute 82.0%

6-(4-Bromo-2-methyl-phenylamino)-7-fluoro-3-(4-oxo-butyl)-3H benzoimidazole-5-carboxylic acid cyclopropylmethoxy-amide

Ausbeute 82.0%

Lösungsmittel

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with NaHCO3, and brine
2. 2
   TrocknenThe organic layer is dried (Na2SO4)
3. 3
   Einengenconcentrated under reduced pressure
4. 4
   Sonstigeto give an orange solid
5. 5
   SonstigePurification by FCC
6. 6
   Wascheneluted with 4:1 methylene chloride/MeOH

Vorschrift

To a mixture of 6-(4-bromo-2-methyl-phenylamino)-3-(4,5-dihydroxy-pentyl)-7-fluoro-3H-benzoimidazole-5-carboxylic acid cyclopropylmethoxy-amide 11 m (0.244 g, 0.456 mmol), THF (5 mL) and pH 7 phosphate buffer (3 mL) is added sodium periodate (0.195 g, 0.911 mmol). After 16 hours, the reaction mixture is diluted with ethyl acetate and washed with NaHCO3, and brine. The organic layer is dried (Na2SO4) and concentrated under reduced pressure to give an orange solid. Purification by FCC eluted with 4:1 methylene chloride/MeOH yields 0.189 g (82%) pure desired product as a yellow solid: MS APCI (+) m/z 505, 503 (M+1 Br pattern) detected; MS APCI (−) m/z 503, 501 (M−1 Br pattern) detected.

Quelle