Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | L-Tyrosine | HCID 6057 | — |
| Reactant | p-Xylyl bromide | HCID 7721 | — |
| Catalyst | Copper Sulfate | HCID 24462 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Sodium Hydroxide | HCID 14798 | — |
| Product | HCID 70061470 | HCID 70061470 | 70% |
Reaction Steps
A mixture of tyrosine (1.83 g, 10 mmol) and CuSO4 (0.81 g, 5 mmol) in 10 mL of 2N NaOH and 5 mL H2O was heated to 60° C. and cooled to room temperature. The reaction mixture was treated with MeOH (35 mL) and 2N NaOH (1.5 mL) followed by α-bromo-p-xylene. The resulting mixture was stirred at 25° C. for 2 hours and filtered. The solid obtained was washed with a 17.5:5 H2O/MeOH solution followed by MeOH. The solid was triturated with 1N HCl (3×10 mL), H2O (2×5 mL), 1.5N NH4OH solution (3×10 mL), and H2O (2×5 mL). The solid obtained was dried overnight under vacuum to give the title compound as a solid (1.99 g, 70%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06423689B1 |
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| Source dataset | uspto-grants-2002_07 |
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| ORD ID | ord-ac41cc469a1845a5bfc246ed8ba1fec7 |
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| Source note | uspto-grants-2002_07 |
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