반응 #488787

반응 방정식

4-(2-isothiocyanato-ethyl)-morpholine

L-tryptophan methyl ester hydrochloride

triethyl amine

→

893-17

수율 83.0%

5-(1H-Indol-3-ylmethyl)-3-(2-morphlin-4-yl-ethyl)-2-thioxo-imidazolidin-4-one

수율 83.0%

용매

dichloromethane

반응 조건

후처리

1. 1
   농축concentrated
2. 2
   기타The residue obtained
3. 3
   기타was purified by column chromatography on silica gel using 60% ethyl acetate-hexane

실험 절차

To a solution of L-tryptophan methyl ester hydrochloride (0.250 mg, 0.001 mol.) in dichloromethane (10 mL) was added triethyl amine (3.0 eq.) followed by 4-(2-isothiocyanato-ethyl)-morpholine (0.190 gm, 0.0011 mol.). The reaction mixture was stirred at room temperature for 24 hr, and then concentrated. The residue obtained was purified by column chromatography on silica gel using 60% ethyl acetate-hexane to give 893-17 (292 mg, 83%): mp 167-169° C., 1H NMR (500 MHz, CDCl3): 2.45-2.51 (m, 6H), 3.02-3.07 (dd, J=9.5 and 15.0 Hz, 1H), 3.46-3.50 (dd, J=4.0 and 15.0 Hz, 1H), 3.65 (m, 4H) 3.89 (d, J=7.0 Hz, 2H), 4.35-4.38 (m, 1H), 6.38 (s, 1H), 7.12 (d, J=2.5 Hz, 1H), 7.16-7.19 (m, 1H), 7.23-7.25 (dd, J=1.5 and 8.0 Hz, 1H), 7.39 (d, J=8.5 Hz, 1H), 7.61 (d, J=8.5 Hz, 1H), 8.15 (s, 1H).

출처