반응 #83120

반응 방정식

trans(-)-2-chlorocyclohexyl chloroformate

α-methyl-DL-tryptophylphenethylamide

triethylamine

→

title compound

수율 81.0%

(±)-Trans-2-chlorocyclohexyl [1-(1H-indol-3-ylmethyl)-1-methyl-2-oxo-2-[(2-phenylethyl)amino]ethyl]carbamate

수율 81.0%

용매

THF

THF

THF

반응 조건

후처리

1. 1
   기타The solvent was removed in vacuo
2. 2
   세척washed successively with 1M aqueous citric acid (2×20 mL), saturated NaHCO3 solution (2×20 mL), 1M NaOH solution (20 mL) and water (4×20 mL)
3. 3
   건조The organic phase was dried over MgSO4
4. 4
   여과filtered
5. 5
   기타Removal of the solvent
6. 6
   workup.DISTILLATIONby vacuum distillation

실험 절차

To a stirred solution of trans(-)-2-chlorocyclohexyl chloroformate (0.16 g, 0.75 mmol ) in anhydrous THF (5 mL) at room temperature was added dropwise a solution of α-methyl-DL-tryptophylphenethylamide (0.23 g, 0.7 mmol) in THF (5 mL), followed by a solution of triethylamine (0.07 g, 0.7 mmol) in THF (5 mL). The reaction was complete after 30 minutes by thin layer chromatographic analysis. The solvent was removed in vacuo and the residue taken up in ethyl acetate (30 mL) and washed successively with 1M aqueous citric acid (2×20 mL), saturated NaHCO3 solution (2×20 mL), 1M NaOH solution (20 mL) and water (4×20 mL). The organic phase was dried over MgSO4 and filtered. Removal of the solvent by vacuum distillation gave the title compound (0.273 g, 81%), a white solid crystallized from ether-hexane, mp 69°-78° C. (ether-hexane); IR (film) 1709 and 1656 cm-1 ; NMR (CDCl3) δ1.2-1.4 (3H, m), 1.54 (3H, s), 1.6-1.8 (3H, m), 2.03-2.23 (2H, m), 2.63-2.69 (2H, m), 3.2-3.5 (4H, m), 3.72-3.79 (1H, m), 4.67-4.73 (1H, m), 5.23 (1H, br.s), 6.1-6.2 (1H, m), 7.0-7.6 (10H, m), 8.08 (1H, br.s); Anal. (C27H32N3O3Cl), C, H, Cl, N.

출처