Calcium hydride → Ureidovaline

Participants

Reaction Conditions

Reaction Steps

To a suspension of calcium hydride (o.98 g, 23.2 mmol) in THF (25 mL) at 0° C. to 5° C. was added 3.94 g (23.1 mmol) of N-methyl-N-((2-isopropyl-4-thiazolyl)methyl)amine. To this was added a solution of N-phenoxycarbonyl-L-Valine (5.0 g, 21.1 mmol) in 20 mL of THF. Following a 5 mL THF rinse, 4.0 mL of water was added, and the reaction mixture was allowed to warm to 20° C. with stirring. After 2 hours, HPLC analysis (t=12.6 min; HPLC conditions: 65% 0.03M KH2PO4 buffer/35% acetonitrile; pH=4; 5μ nucleosil; 4.6×250 mm; 1 mL/min; 205 nm) indicated that the reaction was complete and the desired product had been formed.

Provenance & Evidence