Iodine → N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-iodo-L-phenylalanine ethyl ester

HRID 1188750Notes

Reaction equation

HRID 1188750 reaction equation
II.FC(F)(F)C(OC1C(OC(=O)C(F)(F)F)=C([I:14])C=CC=1)=O.O=C([C@H](CC1C=C(O)C(O)=CC=1)N)O.[CH2:38]([O:40][C:41](=[O:74])[C@H:42]([CH2:51][C:52]1[CH:57]=[CH:56][C:55]([O:58][C:59]([O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:60])=[C:54]([O:66][C:67]([O:69][C:70]([CH3:73])([CH3:72])[CH3:71])=[O:68])[CH:53]=1)[NH:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH3:39]>ClCCl>[CH2:38]([O:40][C:41](=[O:74])[C@H:42]([CH2:51][C:52]1[C:57]([I:14])=[CH:56][C:55]([O:58][C:59]([O:61][C:62]([CH3:63])([CH3:64])[CH3:65])=[O:60])=[C:54]([O:66][C:67]([O:69][C:70]([CH3:73])([CH3:72])[CH3:71])=[O:68])[CH:53]=1)[NH:43][C:44]([O:46][C:47]([CH3:48])([CH3:49])[CH3:50])=[O:45])[CH3:39]

Participants

6

Reactant 4

HCID 807IodineHCID 6047LevodopaHCID 10697409N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-L-phenylalanine ethyl esterHCID 12041285Bistrifluoroacetoxyiodobenzene

Product 1

HCID 10651861N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-iodo-L-phenylalanine ethyl esterYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Iodine (7.4 mmol) and bis(trifluoroacetoxy)iodobenzene (8.16 mmol) were added to a solution of the tri-boc protected dopa analog 14 (5.7 mmol) in anhydrous dichloromethane (60 mL) under argon. (t-Boc, or Boc, stands for (t)ert-(B)ut(O)xy(c)arbonyl.) The reaction mixture was stirred at room temperature for 40 min and then quenched with a saturated solution of sodium thiosulfate. The organic layer was washed with water (3×10 mL), dried with anhydrous sodium sulfate, filtered and evaporated in rotary evaporator. The product was purified by silica gel column chromatography using 15-20% ethyl acetate in hexane as the mobile phase to give the iodo analog, N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-iodo-L-phenylalanine ethyl ester 15, as white foam in 77% yield.

Workup

  1. customquenched with a saturated solution of sodium thiosulfate
  2. washThe organic layer was washed with water (3×10 mL)
  3. dry with materialdried with anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated in rotary evaporator
  6. customThe product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4d638140d3ca4efca9628922d3d4bb66
Source dataset
uspto-grants-2014_03
Patent number
US08674101B2

Reaction notes

Loading…