3',5'-Diiodo-L-tyrosine → tert-butyl (2S)-2-amino-3-(4-hydroxy-3,5-diiodophenyl)propanoate

HRID 429923Notes

Reaction equation

HRID 429923 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([I:15])[C:13]=1[OH:14])[CH2:5][C@@H:6]([C:8]([OH:10])=[O:9])[NH2:7].C([O-])(O)=O.[Na+]>C(OC(C)(C)C)(=O)C>[I:1][C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([I:15])[C:13]=1[OH:14])[CH2:5][C@@H:6]([C:8]([O:10][C:4]([CH3:11])([CH3:5])[CH3:3])=[O:9])[NH2:7]

Participants

4

Reactant 2

HCID 93053',5'-Diiodo-L-tyrosineHCID 516892Sodium Bicarbonate

Product 1

HCID 54479509tert-butyl (2S)-2-amino-3-(4-hydroxy-3,5-diiodophenyl)propanoateYield 148.7%

Reagents, catalysts & solvents 1

HCID 10908tert-Butyl acetateSolvent

Procedure

A solution of 5.0 g of 3,5-diiodo-L-tyrosine and 0.95 mL of 70% aqueous HClO4 in 155 mL of tert-butyl acetate was stirred at RT under nitrogen for 4 days. The solution was neutralized by addition of 150 mL of 5% aqueous NaHCO3 and the mixture was subjected to rotary evaporation to remove tert-butyl acetate. An off-white precipitate resulted which was collected by filtration and dried in vacuo. The crude product was subjected to flash chromatography on silica gel (97:3 CH2Cl2:MeOH) to afford 4.2 g (75%) of tert-butyl 3,5-diiodo-L-tyrosinate as a white powder, m.p. 165-168° C.

Workup

  1. customthe mixture was subjected to rotary evaporation
  2. customto remove tert-butyl acetate
  3. customAn off-white precipitate resulted which
  4. filtrationwas collected by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-71e642d5c24a4be59e211a4cdc9deed2
Source dataset
uspto-grants-2001_11
Patent number
US06319702B1

Reaction notes

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