Iodine → 4-Iodophenylalanine

Temperature

35 °C

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 NalO3 while stirring. The reaction mixture was stirred at 70° C. for 21 h, during this time, two portions of 1 gm of NalO3 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.

1. stirringThe reaction mixture was stirred at 70° C. for 21 h, during this time, two portions of 1 gm of NalO3
2. additionwere added
3. temperatureThe mixture was cooled
4. customthe acetic acid was removed
5. additionthe residue oil was diluted
6. additionby adding 400 mL of water
7. extractionThe aqueous solution was extracted once with 100 mL ether and once with 100 of dichloromethane
8. additionby adding solid NaOH
9. customto precipitate the crude product, which
10. temperatureafter chilling
11. filtrationwas filtered
12. washrinsed with 800 mL of water and 300 mL of ethanol
13. customThe wet product was recrystallized from 200 mL of acetic acid

ORD record

ord-c183766c195a4f149afee786a703af69

Source dataset

uspto-grants-2008_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07384749B2