Hydrochloric Acid → HCID 86598311, compound

HRID 1393366Notes

Reaction equation

HRID 1393366 reaction equation
FC(F)(F)C(O)=O.C[O:9][C:10](=[O:34])[C@H:11]([CH2:20][C:21]1[CH:26]=[C:25]([I:27])[C:24]([O:28][CH2:29][CH2:30][CH2:31][Br:32])=[C:23]([I:33])[CH:22]=1)[NH:12]C(OC(C)(C)C)=O.O.[OH-].[Li+].Cl>O1CCCC1.O>[Br:32][CH2:31][CH2:30][CH2:29][O:28][C:24]1[C:23]([I:33])=[CH:22][C:21]([CH2:20][C@@H:11]([C:10]([OH:34])=[O:9])[NH2:12])=[CH:26][C:25]=1[I:27]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 168937Lithium hydroxide, monohydrateHCID 69316249HCID 69316249, compound

Product 1

HCID 86598311HCID 86598311, compoundYield 72.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Trifluoroacetic acid (2 ml) was added to O-(3-bromo-propyl)-N-t-butoxycarbonyl-3,5-diiodo-L-tyrosine methyl ester (131mg, 0.196 mmol) and the mixture was stirred at room temperature for 8 hrs. The solvent of the reaction mixture was distilled off under reduced pressure. The residue was dissolved in tetrahydrofuran (2 ml)-water (2 ml) and lithium hydroxide monohydrate (25 mg, 0.596 mmol) was added thereto with stirring under ice cooling. The mixture was stirred at the same temperature for 4.5 hrs. To the reaction mixture were added 1N hydrochloric acid (0.2 ml) and water (5 ml), and the mixture was stirred at room temperature for 30 min. The precipitates were collected by filtration, washed with water and dried under reduced pressure to give O-(3-bromopropyl)-3,5-diiodo-L-tyrosine(79 mg, 71%) as colorless crystals.

Workup

  1. distillationThe solvent of the reaction mixture was distilled off under reduced pressure
  2. additionwas added
  3. stirringwith stirring under ice cooling
  4. stirringThe mixture was stirred at the same temperature for 4.5 hrs
  5. stirringthe mixture was stirred at room temperature for 30 min
  6. filtrationThe precipitates were collected by filtration
  7. washwashed with water
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-1b94205260d44b1a93bdd885320a78f4
Source dataset
uspto-grants-2008_03
Patent number
US07345068B2

Reaction notes

Loading…