Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Lithium hydroxide, monohydrate | HCID 168937 | — |
| Reactant | HCID 69316249 | HCID 69316249 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86598311 | HCID 86598311 | 72.8% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07345068B2 |
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| Source dataset | uspto-grants-2008_03 |
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| ORD ID | ord-1b94205260d44b1a93bdd885320a78f4 |
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| Source note | uspto-grants-2008_03 |
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