Iodine → N-formyl-3,4-dimethoxy-6-iodo-L-phenylalanine ethyl ester

HRID 275521Notes

Reaction equation

HRID 275521 reaction equation
[I:1]I.[CH2:3]([O:5][C:6](=[O:22])[C@H:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=1)[NH:8][CH:9]=[O:10])[CH3:4]>C(Cl)Cl.FC(F)(F)C([O-])=O.[Ag+]>[CH2:3]([O:5][C:6](=[O:22])[C@H:7]([CH2:11][C:12]1[C:17]([I:1])=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=1)[NH:8][CH:9]=[O:10])[CH3:4]

Participants

5

Reactant 2

HCID 807IodineHCID 10945877N-formyl-3,4-dimethoxy-L-phenylalanine ethyl ester

Product 1

HCID 11122367N-formyl-3,4-dimethoxy-6-iodo-L-phenylalanine ethyl esterYield 75.3%

Reagents, catalysts & solvents 2

HCID 76299Silver trifluoroacetateCatalystHCID 6344DichloromethaneSolvent

Procedure

Iodine (2.1 g, 8.3 mmol) was added to a solution of dimethoxy derivative 2 (2.1 g, 7.5 mmol) and silver trifluoroacetate (2.0 g, 9.1 mmol) in methylene chloride (110 mL) and the reaction mixture was stirred at room temperature for 48 h. The yellow precipitate that formed was filtered and washed with methylene chloride. The combined filtrates were washed with 1M Na2S2O5 (2×75 mL), water (2×75 mL), dried and concentrated under reduced pressure to give a solid residue. Recrystallization of this residue from ethyl acetate and petroleum ether gave a white solid 3 (2.3 g, 75%); m.p. 151°-152° C.

Workup

  1. customThe yellow precipitate that formed
  2. filtrationwas filtered
  3. washwashed with methylene chloride
  4. washThe combined filtrates were washed with 1M Na2S2O5 (2×75 mL), water (2×75 mL)
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customto give a solid residue
  8. customRecrystallization of this residue from ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-41f614f33f9049788b0b5e1e6c9b4ab4
Source dataset
uspto-grants-1995_02
Patent number
US05393908

Reaction notes

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