Triethylamine → BOC-D-alanine

Participants

Reaction Steps

To a mixture of Z--(L)--mesoDAP (2) (1.50 g) and triethylamine (1.0 g) in aqueous dioxane (dioxane 30 ml and water 20 ml) was added Boc--D--Ala--OSu (3) (1.32 g) and the mixture was allowed to stand overnight at room temperature. Dioxane was evaporated, and the resulting aqueous solution was acidified with diluted hydrochloric acid and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and evaporated to give Boc--D--Ala--(D)--Z--(L)--mesoDAP (4) (1.90 g) as a white foam.

Provenance & Evidence