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

HRID 403006Notes

Reaction equation

HRID 403006 reaction equation
II.FC(F)(F)C(OC1C(OC(=O)C(F)(F)F)=C([I:14])C=CC=1)=O.[CH2:24]([O:26][C:27](=[O:60])[C@H:28]([CH2:37][C:38]1[CH:43]=[CH:42][C:41]([O:44][C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])=[C:40]([O:52][C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[CH:39]=1)[NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH3:25]>ClCCl>[CH2:24]([O:26][C:27](=[O:60])[C@H:28]([CH2:37][C:38]1[C:43]([I:14])=[CH:42][C:41]([O:44][C:45]([O:47][C:48]([CH3:49])([CH3:50])[CH3:51])=[O:46])=[C:40]([O:52][C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[CH:39]=1)[NH:29][C:30]([O:32][C:33]([CH3:34])([CH3:35])[CH3:36])=[O:31])[CH3:25]

Participants

5

Reactant 3

HCID 807IodineHCID 10697409HCID 10697409, compoundHCID 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 ester analog 16 (5.7 mmol) in anhydrous dichloromethane (60 mL) under argon. 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 a 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 17 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 a rotary evaporator
  6. customThe product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-54bccd3478a245e99a84724a2d820c52
Source dataset
uspto-grants-2014_06
Patent number
US08742139B2

Reaction notes

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