反应详情

1-Hydroxybenzotriazole (546 mg, 4.0 mmol), C-(1H-indol-3-yl)methylamine (292 mg, 2.0 mmol) and N-methylmorpholine (0.444 ml, 4.0 mmol) were added to a solution of (4-dimethylamino-4-phenylcyclohexyl)acetic acid hydrochloride (596 mg, 2.0 mmol) in dry dimethylformamide under argon. Dicyclohexylcarbodiimide (834 mg, 4.0 mmol) was added at 0° C. and the mixture was stirred at RT for 7 d. Working up of the mixture was carried out by separating off the urea which had precipitated out and introducing the filtrate into a mixture of saturated NaCl solution (40 ml) and saturated NaHCO3 solution (10 ml). A mixture of urea and product thereby precipitated out (482 mg) and was separated off. The filtrate obtained was diluted with water (300 ml), 5 M sodium hydroxide solution (4 ml, 20 mmol) was added and the mixture was stored at 5° C. for 16 h. A crude product thereby precipitated out as a beige-coloured substance (234 mg), which was separated off by filtration. After purification of the two product fractions by chromatography on silica gel with EA/methanol (4:1) and methanol, the product was isolated as a beige-coloured solid in a yield of 30% (230 mg).

1. customby separating off the urea which
2. customhad precipitated out
3. additionintroducing the filtrate
4. additioninto a mixture of saturated NaCl solution (40 ml) and saturated NaHCO3 solution (10 ml)
5. additionA mixture of urea and product
6. customthereby precipitated out (482 mg)
7. customwas separated off
8. customThe filtrate obtained
9. additionwas added
10. waitthe mixture was stored at 5° C. for 16 h
11. customA crude product thereby precipitated out as a beige-coloured substance (234 mg), which
12. customwas separated off by filtration
13. customAfter purification of the two product fractions by chromatography on silica gel with EA/methanol (4:1) and methanol
14. customthe product was isolated as a beige-coloured solid in a yield of 30% (230 mg)