L-Valine → Ureidovaline

Participants

Reaction Steps

To a stirred slurry of anhydrous 95% NaH (500 mg, 20.8 mmol) at -10° C. in 25 mL of THF was added N-phenoxycarbonyl-L-Valine (4.93 g, 20.8 mmol) followed by a 10 mL THF rinse keeping the temperature <0° C. using an ice-water bath. Following the addition of the N-protected Valine, N-methyl-N-((2-isopropyl-4-thiazolyl)methyl)amine (3.54 g, 20.8 mmol) was added at <0° C. The reaction was allowed to warm to ambient temperature. After 3 hours, 50 mL of THF was added followed by 25 mg (1 mmol) of NaH. After 16 hours at room temperature, the reaction was complete. The reaction was worked up by the procedures described in Example 1.

Provenance & Evidence