Iodine → 2-Iodo-4-nitro-l-phenylalanine

HRID 369813

Reaction equation

HRID 369813 reaction equation
[I:1]I.[N+:3]([C:6]1[CH:17]=[CH:16][C:9]([CH2:10][C@@H:11]([C:13]([OH:15])=[O:14])[NH2:12])=[CH:8][CH:7]=1)([O-:5])=[O:4].S([O-])([O-])(=O)=S.[Na+].[Na+]>S(=O)(=O)(O)O>[I:1][C:8]1[CH:7]=[C:6]([N+:3]([O-:5])=[O:4])[CH:17]=[CH:16][C:9]=1[CH2:10][C@@H:11]([C:13]([OH:15])=[O:14])[NH2:12]

Participants

5

Reactant 3

HCID 807IodineHCID 137064-Nitro-3-phenyl-L-alanineHCID 24477Sodium Thiosulfate

Product 1

HCID 545742802-Iodo-4-nitro-l-phenylalanine

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A 250 mL round bottomed flask equipped with a magnetic stirrer was charged with 60 mL of fuming sulfuric acid (Aldrich) and 12.1 g of iodine (Aldrich). To the resulting dark red solution was added 10.0 g of 4-nitro-L-phenylalanine by slow addition. The flask was fitted with a CaCl2 drying tube and the reaction mixture was stirred at RT for 18 h. The mixture was then poured onto 300 g of crushed ice. A yellow-brown emulsion resulted which was treated with 7.4 g of sodium thiosulfate and stirred. The resulting light brown suspension was basified to pH=9 by addition of solid NaCO3. This was followed by acidification to pH=5.5 by addition of conc. H3SO4. A brown solid precipitated which was collected by filtration and dried in vacuo. This afforded 6.54 g (41%) of 2-iodo-4-nitro-L-phenylalanine as a brown powder, m.p.>200° C.

Workup

  1. customA 250 mL round bottomed flask equipped with a magnetic stirrer
  2. additionby slow addition
  3. customThe flask was fitted with a CaCl2 drying tube
  4. customA yellow-brown emulsion resulted which
  5. stirringstirred
  6. additionThis was followed by acidification to pH=5.5 by addition of conc. H3SO4
  7. customA brown solid precipitated which
  8. filtrationwas collected by filtration
  9. customdried in vacuo

Sources & evidence

ORD record
ord-95a36f2ae0334c89a3258145c6c2a242
Source dataset
uspto-grants-2000_10
Patent number
US06140100

Linked notes

Loading…