Reaktion #1882146

Reaktionsgleichung

(thymin-1-yl)-acetic acid

1-(2-nitro-benzenesulfonyl)-3-methyl-piperazin-2-one HCl salt

PyBOP

N,N-diisopropylethylamine

→

titled compound

Ausbeute 72.0%

3-Methyl-1-(2-nitro-benzensulfonyl)-4-[(thymin-1-yl)acetyl]-piperazin-2-one

Ausbeute 72.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenthe reaction mixture was concentrated under reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane
3. 3
   Waschenwashed with water
4. 4
   TrocknenThe organic layer was dried over anhydrous sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   EinengenThe filtrate was concentrated in reduced pressure
7. 7
   Sonstigethe residue was purified by column chromatography

Vorschrift

To a solution of (thymin-1-yl)-acetic acid (55 mg, 0.30 mmol), 1-(2-nitro-benzenesulfonyl)-3-methyl-piperazin-2-one HCl salt (100 mg, 0.30 mmol), and PyBOP (156 mg, 0.45 mmol) in DMF (1 mL) was added N,N-diisopropylethylamine (0.08 mL) at room temperature. After stirring for additional 2 h at 40° C., the reaction mixture was concentrated under reduced pressure. The residue was dissolved in dichloromethane and washed with water. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in reduced pressure and the residue was purified by column chromatography to give the titled compound (100 mg, 72%). 1H NMR (500 MHz; DMSO-d6) δ 11.31 (s, 1H), 8.33 (d, 1H), 8.10 (d, 1H), 8.04˜7.93 (m, 2H), 7.35 (s, 1H), 4.85˜4.60 (m, 2.5H), 4.55˜4.40 (m, 0.5H), 4.20˜4.10 (m, 0.5H), 4.05˜3.90 (m, 1.5H), 3.78˜3.60 (m, 1H), 3.30 (m, 1H), 1.74 (s, 3H), 1.42 (d, 1H), 1.27 (d, 2H).

Quelle