Hydantoins: The Synthesis of Thiotyrosine

The Chemistry of the Hydantoins.

“…The C-5 unsaturated hydantoin derivatives obtained as a result of condensation reactions may be reduced by any of a number of common reducing agents. Among those most frequently used are hydrogen iodide and red phosphorus (629), sodium amalgam (362,367), and ammonium sulfide (95); other reagents include aluminum amalgam (629), hydrogen iodide in glacial acetic acid (630), tin and hydrochloric acid (367), tin and hydrogen chloride in ethanol (378), and hydrogen sulfide dissolved in pyridine, or in aqueous solutions of sodium or barium sulfide (95). Catalytic reductions have also been carried on, using palladium in alcohol (281) or Raney nickel in sodium hydroxide (206).…”

“…ß-Phenylalanine........... (629) (407) ß-Piperonylalanine......... (184) ß-Pyridylalanine........... (483) (417) ß-Quinolylalanine.......... (505) (171) ß-2-Thienylalanine......... (39,202) Thiotyrosine.............. (367) (387) Through the hydrolysis of appropriately substituted hydantoins, other imidodiacetic acids have been prepared by D. A. Hahn and her associates, including tyrosine-A-phenylacetic acid (275), and the A-acetic and A-phenylacetic acid derivatives of /3-phenylalanine (283).…”

Analogs of Phenylalanine Containing Sulfur

“…1 Recrystallized from 20% HC1. 5 Recrystallized from water. * Recrystallized from water-ethanol mixture.…”