反応 #83120

反応方程式

trans(-)-2-chlorocyclohexyl chloroformate

α-methyl-DL-tryptophylphenethylamide

triethylamine

→

title compound

収率 81.0%

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

収率 81.0%

溶媒

THF

THF

THF

反応条件

後処理

1. 1
   その他The solvent was removed in vacuo
2. 2
   洗浄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)
3. 3
   乾燥The organic phase was dried over MgSO4
4. 4
   ろ過filtered
5. 5
   その他Removal of the solvent
6. 6
   workup.DISTILLATIONby vacuum distillation

実験手順

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.

出典