[13139-12-3] · C9H13NO5 · N-(t-Butoxycarbonyloxy)succinimide · (MW 215.21)
(reagent for the protection of amino groups, including amino acids2)
Alternate Name: Boc-OSu.
Physical Data: mp 98-100 °C.1
Solubility: sol ether, ethyl acetate, acetone; insol water, petroleum ether.
Form Supplied in: white solid, widely available.
Handling, Storage, and Precautions: stable under normal storage conditions. No known toxicity.
N-(t-Butoxycarbonyloxy)succinimide (Boc-OSu) has been developed to supplement the unstable t-Butyl Chloroformate for the protection of amino compounds and especially of amino acids. The reagent is a stable compound easily prepared from t-butanol and N-oxysuccinimide chloroformate1 and has been used for the protection of various compounds including amino acids, peptides,2 proteins,3,4 and amino saccharides.5 N-Oxysuccinimide carbonates have been shown to give very pure N-protected amino acids with a particularly low content of dipeptide byproduct.6 It is also noteworthy that both the Boc and the OSu groups can be introduced into amino acids almost simultaneously in a one-pot synthesis of Boc-protected N-oxysuccinimide active esters of amino acids (eq 1).7
Attempts to protect a-hydrazino acids regioselectively led to almost no discrimination between N-a and N-b protection, compared to the very good regioselectivity observed with benzyloxycarbonyloxysuccinimide (eq 2).8
SNPE, Vert-le-Petit, France