반응 #327039

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N-[(1S)-1-cyano-2-(4-iodophenyl)ethyl]-4-fluoro-N2-{(1S)-2,2,2-trifluoro-1-[4′-(methylsulfonyl)biphenyl-4-yl]ethyl}-L-leucinamide

water

DMF

→

(S)-4-Fluoro-4-methyl-2-[(S)-2,2,2-trifluoro-1-(4′-methanesulfonyl-biphenyl-4-yl)-ethylamino]-pentanoic acid [(S)-1-cyano-2-(4-cyano-phenyl)-ethyl]-amide

반응 조건

후처리

1. 1
   기타N2 was bubbled into the mixture for 5 minutes
2. 2
   온도The reaction mixture was cooled
3. 3
   workup.ADDITIONdiluted with EtOAc and saturated aqueous ammonium chloride
4. 4
   추출the aqueous layer was extracted with EtOAc
5. 5
   세척The combined organic layers were washed with brine and water
6. 6
   여과filtered
7. 7
   농축concentrated
8. 8
   기타The crude compound was purified by automated SiO2 flash chromatography system

실험 절차

To N-[(1S)-1-cyano-2-(4-iodophenyl)ethyl]-4-fluoro-N2-{(1S)-2,2,2-trifluoro-1-[4′-(methylsulfonyl)biphenyl-4-yl]ethyl}-L-leucinamide (1 eq) in DMF (0.1 M) were added Pd2(dba)3 (0.05 eq), dppf (0.05 eq), water (10 eq) and zinc cyanide (2.5 eq). N2 was bubbled into the mixture for 5 minutes and the mixture was then heated to 90° C. for 2 h. The reaction mixture was cooled and diluted with EtOAc and saturated aqueous ammonium chloride, the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine and water, filtered and concentrated. The crude compound was purified by automated SiO2 flash chromatography system using solvent gradient of 40% EtOAc/Hex to 100% EtOAc/Hex.

출처