Sodium Iodide → HCID 86598320, compound

HRID 1393376Notes

Reaction equation

HRID 1393376 reaction equation
C[Si](Cl)(C)C.[CH3:6][O:7][C:8](=[O:44])[C@H:9]([CH2:17][C:18]1[CH:23]=[C:22]([Cl:24])[C:21]([O:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([O:34][C:35]3[CH:40]=[CH:39][C:38]([O:41]C)=[CH:37][CH:36]=3)[CH:29]=2)=[C:20]([Cl:43])[CH:19]=1)[NH:10][C:11](=[O:16])[C:12]([F:15])([F:14])[F:13].[I-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C.O>[CH3:6][O:7][C:8](=[O:44])[C@H:9]([CH2:17][C:18]1[CH:23]=[C:22]([Cl:24])[C:21]([O:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([O:34][C:35]3[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=3)[CH:29]=2)=[C:20]([Cl:43])[CH:19]=1)[NH:10][C:11](=[O:16])[C:12]([F:15])([F:14])[F:13]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 24477Sodium ThiosulfateHCID 86598321HCID 86598321, compound

Product 1

HCID 86598320HCID 86598320, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Trimethylsilyl chloride (0.25 ml, 1.97 mmol) was added dropwise to a solution of 3,5-dichloro-N-trifluoroacetyl-O-[2-[3-(4-methoxyphenoxy)phenyl]ethyl]-L-tyrosine methyl ester (190 mg, 0.324 mmol) and sodium iodide (292 mg, 1.95 mmol) in acetonitrile (3 ml) at room temperature. The mixture was stirred under argon atmosphere at room temperature for 22 hrs. and then heated under reflux for 9 hrs. The reaction mixture was poured into water (30 ml) and 10% aqueous sodium thiosulfate (20 ml) was added thereto. The mixture was extracted with ethyl acetate and the extract was washed with brine and then dried. The solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=3) to give 3,5-dichloro-N-trifluoroacetyl-O-[2-[3-(4-hydroxyphenoxy)-phenyl]ethyl]-L-tyrosine methyl ester (120 mg, 65%) as a colorless oil.

Workup

  1. temperatureand then heated
  2. temperatureunder reflux for 9 hrs
  3. additionwas added
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe extract was washed with brine
  6. customdried
  7. distillationThe solvent was distilled off under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=3)

Sources & evidence

ORD record
ord-80aeca94f25241bb9bb598b523d021e5
Source dataset
uspto-grants-2008_03
Patent number
US07345068B2

Reaction notes

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