Reaktion #2831

Reaktionsgleichung

1-hydroxybenzotriazole

1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride

morpholine

compound ( [5]-(53)-278 )

4-methyl-3-nitrobenzoic acid

→

crystals

4-methyl-3-nitrobenzoic acid morpholide

Lösungsmittel

triethylamine

water

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto obtain a homogeneous solution
2. 2
   EinengenThe solution was concentrated
3. 3
   workup.DISSOLUTIONThe residue was dissolved in chloroform
4. 4
   Waschenthe solution was washed with 1N HCl aqueous solution and saturated brine
5. 5
   TrocknenThe organic layer was dried over anhydrous sodium sulfate
6. 6
   Einengenconcentrated

Vorschrift

The compound ([5]-(53)-278) (6.5272 g) prepared in Example 72 was dissolved in anhydrous DMF (98 ml). Then, 1-hydroxybenzotriazole (6.3297 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (8.9795 g), triethylamine (6.5 ml), and morpholine (4.1 ml) were added to the solution. The mixture was stirred at room temperature for 4 hours. A small amount of water was added to the resulting yellowish orange solution including the white salt to obtain a homogeneous solution. The solution was concentrated. The residue was dissolved in chloroform, and the solution was washed with 1N HCl aqueous solution and saturated brine. The organic layer was dried over anhydrous sodium sulfate, and concentrated to obtain yellowish brown crystals (8.9903 g). The product was recrystallized from n-hexane/ethyl acetate to obtain the above-captioned compound ([5]-(54)-278) (7.8455 g) as light yellow crystals.

Quelle