반응 #7148

반응 방정식

potassium iodide

Cesium carbonate

(1R,2S)-2-(4-Chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid amide

4-Chloromethyl-N-ethylbenzamide

→

4-[[(1R,2S)-(2-Carbamoyl-cyclohexyl)-(4-chlorobenzenesulfonyl)-amino]-methyl]-N-ethyl benzamide

수율 40.5%

용매

DMF

ethyl acetate

반응 조건

후처리

1. 1
   기타Reaction
2. 2
   기타Reaction mixture
3. 3
   세척then was washed with water (2×15 mL)
4. 4
   농축Organic layer was concentrated in vacuo
5. 5
   기타Residue was purified by preparatory HPLC (acetonitrile/water/trifluoroacetic acid)
6. 6
   기타Acetonitrile was removed from the mixture in vacuo
7. 7
   온도Remaining aqueous was frozen

실험 절차

Cesium carbonate (1.4 mmol) was added to a solution of (1R,2S)-2-(4-Chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid amide (0.62 mmol) in DMF (7 mL). 4-Chloromethyl-N-ethylbenzamide (0.76 mmol) was added to the mixture followed by potassium iodide (0.75 mmol). Reaction was stirred at room temperature overnight. Reaction mixture was diluted with ethyl acetate (20 mL) then was washed with water (2×15 mL). Organic layer was concentrated in vacuo. Residue was purified by preparatory HPLC (acetonitrile/water/trifluoroacetic acid). Proper fractions were combined. Acetonitrile was removed from the mixture in vacuo. Remaining aqueous was frozen and lyophilized to yield 4-[[(1R,2S)-(2-Carbamoyl-cyclohexyl)-(4-chlorobenzenesulfonyl)-amino]-methyl]-N-ethyl benzamide (120 mg) as a white solid in 40% yield.: 1H NMR (300 Mz, DMSO-d6) δ 8.40 (t, 1 H), 7.79 (d, 2 H, J=8.4), 7.70 (d, 2 H, J=8.4), 7.64 (d, 2 H, J=8.4 ), 7.32 (d, 2 H, J=8.1), 6.66 (s, 1 H), 4.68 (d, 1 H, J=17.2), 4.54 (d, 1 H, J=17.2), 3.85 (m, 1 H), 3.28 (m, 2 H), 2.78 (s, 1 H), 2.40 (m, 1 H), 1.78 (m, 1 H), 1.63 (m, 2 H), 1.42–1.17 (m, 3 H), 1.12 (t, 3 H), 0.92 (m, 1 H); MS m/e 500 (M+Na)+.

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