반응 #1135525

반응 방정식

1,2-dihydroxypropane

N-((1S,2R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)but-3-enyl)acetamide

pyridine

HCl

oxalyl chloride

→

title compound

(1S,2R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)but-3-en-1-amine

용매

ethanol

THF

반응 조건

후처리

1. 1
   온도the reaction was warmed to rt
2. 2
   온도The reaction mixture was heated at 55° C. for 10 min
3. 3
   온도cooled down to rt
4. 4
   기타was consumed
5. 5
   workup.ADDITION200 ml of ethyl acetate was added
6. 6
   세척the organic layer was washed consecutively with NaHCO3 solution and sat. NaCl solution
7. 7
   건조dried over MgSO4
8. 8
   여과filtered
9. 9
   농축the filtrate was concentrated
10. 10
    기타The crude mixture was purified by flash chromatography on silica gel

실험 절차

To a mixture of 4.1 g (12.27 mmol) of N-((1S,2R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)but-3-enyl)acetamide (Example 115, Step D) and pyridine (1.20 mL, 14.72 mmol) in THF (35.0 mL) was added 1.2 mL (13.5 mmol) of oxalyl chloride at 0° C. The resulting light yellow slurry was stirred at 0° C. for 1.5 h. 1,2-dihydroxypropane (1.80 mL, 24.53 mmol) was added in one portion and the reaction was warmed to rt. The mixture was treated with ethanol (16.0 ml) followed by 6 N HCl (16.0 ml). The reaction mixture was heated at 55° C. for 10 min and then cooled down to rt. When LCMS indicated that most SM was consumed, 200 ml of ethyl acetate was added, and the organic layer was washed consecutively with NaHCO3 solution and sat. NaCl solution, dried over MgSO4, filtered and the filtrate was concentrated. The crude mixture was purified by flash chromatography on silica gel to give the title compound.

출처