反应详情

A mixture of 13.6 g of 4-amino-3,5-dichlorophenacyl bromide and 4.6 g of (R)-1-methyl-3-(4-aminocarbonylphenyl)propylamine in 100 ml of chloroform was warmed to 50° for 3 hours. The mixture was evaporated in vacuo, the residue was dissolved in 200 ml of methanol was 70 ml of water and a solution of 3.0 g of sodium borohydride in 20 ml of water was added dropwise thereto while cooling with ice and stirring so that the temperature did not rise above 20°. After completion of the addition, the mixture was stirred at 5°-10° for a further 2 hours, then poured into ice-water and extracted with methylene chloride. The material isolated from the methylene chloride extract was chromatographed on silica gel. With chloroform/n-propanol/25% ammonia (1000:10:1) there was obtained pure p-[(R)-3-[bis-[(RS)-4-amino-3,5-dichloro-β-hydroxyphenethyl]amino]butyl]benzamide in amorphous form; [α]D20 =-46° (c=1.0% in methanol); ε242 =31080; ε302 =7250.

1. temperaturewas warmed to 50° for 3 hours
2. customThe mixture was evaporated in vacuo
3. dissolutionthe residue was dissolved in 200 ml of methanol
4. additiona solution of 3.0 g of sodium borohydride in 20 ml of water was added dropwise
5. temperaturewhile cooling with ice
6. customdid not rise above 20°
7. additionAfter completion of the addition
8. stirringthe mixture was stirred at 5°-10° for a further 2 hours
9. additionpoured into ice-water
10. extractionextracted with methylene chloride
11. customThe material isolated from the methylene chloride
12. extractionextract
13. customwas chromatographed on silica gel