Triethylamine → HCID 11790997, compound

Participants

Reaction Steps

617 g (3.68 mol) of (S)-valine methyl ester hydrochloride were suspended in about 2.2 l of tetrahydrofuran and 745 g (7.38 mol) of triethylamine were added. 451 g (3.35 mol) of tetrahydrofuran-2-carbonyl chloride in 200 ml of THF were added dropwise with stirring, the reaction temperature rising to about 65° C. After completion of the addition, the mixture was stirred at room temperature for a further 12 hours. The precipitate was filtered off with suction and thoroughly washed with tetrahydrofuran, and the combined organic phases were evaporated. The residue was dissolved in ether to remove excess (S)-valine methyl ester, shaken with water and dried in the customary manner. Vacuum distillation yields N-(2-tetrahydrofuroyl)-(S)-valine methyl ester (formula V with X=S, n=1, R=CH(CH3)2 and R'=CH3) as a colorless liquid, b.p. 98°-103° C./0.01 torr, yield: 611 g (80%).

Provenance & Evidence