반응 #1135530

반응 방정식

trans-beta-styrenesulfonyl chloride

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

N,N-diisopropylethylamine

→

title compound

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

용매

water

DCM

반응 조건

후처리

1. 1
   workup.STIRRINGAfter being stirred for 3.25 hours
2. 2
   추출extracted with DCM
3. 3
   세척The combined organic layers were washed with sat. aq. NaCl solution
4. 4
   건조dried over Na2SO4
5. 5
   여과filtered
6. 6
   농축the filtrate was concentrated
7. 7
   기타Purification by flash chromatography on silica gel (0 to 40% EtOAc in hexanes gradient)

실험 절차

To a solution of 5.33 g (18.24 mmol) of (1S,2R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)but-3-en-1-amine (Example 115, Step E) in DCM (45.0 mL) was added N,N-diisopropylethylamine (4.8 mL, 27.5 mmol), followed by trans-beta-styrenesulfonyl chloride (4.17 g, 20.58 mmol). The resulting solution was stirred at ambient temperature under an N2 atmosphere. After being stirred for 3.25 hours, the reaction was diluted with water and extracted with DCM. The combined organic layers were washed with sat. aq. NaCl solution, dried over Na2SO4, filtered and the filtrate was concentrated. Purification by flash chromatography on silica gel (0 to 40% EtOAc in hexanes gradient) provided the title compound as a yellow solid.

출처