반응 #1911508

반응 방정식

(S)-4-(oxiranylmethoxy)-9H-carbazole

N-(4-[2-aminoethyl]phenyl)benzenesulfonamide

ethanol

→

desired product

수율 29.0%

(S)-4-[2-Hydroxy-3-(2-[4-phenylsulfonamidophenyl]propylamino)propoxy]carbazole

수율 29.0%

반응 조건

후처리

1. 1
   온도The mixture was cooled
2. 2
   농축concentrated in vacuo to an amorphous solid
3. 3
   세척washed once with 1N HCl (20 mL) and twice with aqueous saturated sodium bicarbonate solution and finally with water
4. 4
   건조The organic layer was then dried over anhydrous magnesium sulfate
5. 5
   여과filtered
6. 6
   농축concentrated to dryness
7. 7
   기타The resulting white amorphous product was purified by radial chromatography (Chromatatron)
8. 8
   기타Concentration of the appropriate fractions and drying under vacuum

실험 절차

A stirred mixture of (S)-4-(oxiranylmethoxy)-9H-carbazole (478.5 mg, 2.0 mmol), N-(4-[2-aminoethyl]phenyl)benzenesulfonamide (829.1 mg, 3.0 mmol), acetic acid (1 drop), and ethanol (50 mL) was heated at 45° C. for 16 h with a slow stream of nitrogen bubbling through the reaction mixture. The mixture was cooled and concentrated in vacuo to an amorphous solid. The solid was taken up in ethyl acetate (150 mL) and washed once with 1N HCl (20 mL) and twice with aqueous saturated sodium bicarbonate solution and finally with water. The organic layer was then dried over anhydrous magnesium sulfate, filtered, and concentrated to dryness. The resulting white amorphous product was purified by radial chromatography (Chromatatron) using EtOAc:MeOH (9:1). Concentration of the appropriate fractions and drying under vacuum gave 290 mg (29%) of the desired product as an amorphous white solid. Anal. Calcd. for C29H29N3O4S.0.5 mol H2O: C, 66.39; H, 5.76; N, 8.01. Found: C, 66.49; H, 5.81; N, 7.77.

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