반응 #1914827

반응 방정식

phenylalanine

iodine

→

4-iodo-L-phenylalanine

수율 132.8%

용매

H2SO4

acetic acid

반응 조건

후처리

1. 1
   workup.ADDITIONwere added
2. 2
   온도The mixture was cooled
3. 3
   기타the acetic acid was removed
4. 4
   workup.ADDITIONthe residue oil was diluted
5. 5
   workup.ADDITIONby adding 400 mL of water
6. 6
   추출The aqueous solution was extracted once with 100 mL ether and once with 100 of dichloromethane
7. 7
   workup.ADDITIONby adding solid NaOH
8. 8
   기타to precipitate the crude product, which
9. 9
   온도after chilling
10. 10
    여과was filtered
11. 11
    세척rinsed with 800 mL of water and 300 mL of ethanol
12. 12
    기타The wet product was recrystallized from 200 mL of acetic acid

실험 절차

Into a solution of 40.15 gm (0.243 mol) of phenylalanine in a mixture of 220 mL of acetic acid and 29 mL of concentrated H2SO4 was added 24.65 gm (0.097 mol) of powered iodine and 10. 18 gm (0.051 mol) of powered NaIO3 while stirring. The reaction mixture was stirred at 70° C. for 21 h, during this time, two portions of 1 gm of NaIO3 were added. The mixture was cooled and the acetic acid was removed by using rotavapor while temperature was maintained at 35° C. and the residue oil was diluted by adding 400 mL of water. The aqueous solution was extracted once with 100 mL ether and once with 100 of dichloromethane. After decolorization with 5 gm of Norit, the aqueous solution was neutralized by adding solid NaOH to precipitate the crude product, which, after chilling, was filtered and rinsed with 800 mL of water and 300 mL of ethanol. The wet product was recrystallized from 200 mL of acetic acid to produce 37.5 gm of 4-iodo-L-phenylalanine.

출처