4-Methylmorpholine → HCID 178462203, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5.67 g (30 mmol) of N-t-butoxycarbonyl-L-alanine in 75 ml of acetonitrile is stirred at 0° and 6.36 g (63 mmol) of N-methylmorpholine is added and the mixture cooled to -20° C. Next 3.62 g (30 mmol) of pivaloyl chloride is added and the mixture stirred at -15° C. for 1.5 hrs and a solution cooled to -10° C., containing 3.46 g (15 mmol) of 2-(4-aminophenyl) 4-hydroxy-5-pyrimidine carboxylic acid, 75 ml of acetonitrile, and 4.17 ml (30 mmol) of triethylamine is added. After stirring for 2 hrs at -10° C. the mixture is then kept at room temperature for 18 hrs. The solution is evaporated to near dryness in vacuo and treated with 200 ml of water. The pH is adjusted to 2.8 with citric acid and the product filtered, washed with water and ether, and dried to give 5.8 g of 2-[4-(N-t-butoxycarbonyl-L-alanylamino)phenyl]-4-hydroxy-5-pyrimidine carboxylic acid. [α]D23 -28.5° (cl, pH 7).

Provenance & Evidence