Iodine → 4-Iodo-D-phenylalanine

HRID 747732

Reaction equation

HRID 747732 reaction equation
II.I([O-])(=O)=O.[Na+].[NH2:8][C@@H:9]([C:17]([OH:19])=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.S(=O)(=O)(O)O.[I:25]([O-])(=O)(=O)=O.[Na+]>C(O)(=O)C>[CH:16]1[C:11]([CH2:10][C@@H:9]([NH2:8])[C:17]([OH:19])=[O:18])=[CH:12][CH:13]=[C:14]([I:25])[CH:15]=1

Participants

7

Reactant 5

HCID 807IodineHCID 1118Sulfuric AcidHCID 71567D-PhenylalanineHCID 23667635Sodium periodateHCID 23675764Sodium Iodate

Product 1

HCID 27332794-Iodo-D-phenylalanine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

12.3 g (48 mmol) of iodine and 5.1 g (24 mmol) of sodium iodate were added to 20 g (121 mmol) of D-phenylalanine, 14.5 ml of concentrated sulfuric acid and 110 ml of acetic acid, and they were stirred for 24 hours. After cooling, 0.5 g of sodium periodate was added thereto, and the solvent was evaporated at 35° C. under reduced pressure. Water was added to the reaction mixture and the resultant mixture was washed with dichloromethane trice. The aqueous phase was neutralized with 1 N aqueous sodium hydroxide solution. After cooling, the obtained precipitate was taken by the filtration and then washed with water and ethanol to obtain the crude product.

Workup

  1. temperatureAfter cooling
  2. customthe solvent was evaporated at 35° C. under reduced pressure
  3. additionWater was added to the reaction mixture
  4. washthe resultant mixture was washed with dichloromethane trice
  5. temperatureAfter cooling
  6. filtrationthe obtained precipitate was taken by the filtration
  7. washwashed with water and ethanol

Sources & evidence

ORD record
ord-0cb431196e6046f6bb440ea30534aa12
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Linked notes

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