[159390-26-8] · C13H22N2O4 · (MW 270.32)
(reagent for clean, efficient peptide coupling, esterification and dehydration)
Physical Data: bp 115-125 °C (<1 mmHg); density 1.062 g mL-1
Solubility: most organic solvents.
Form Supplied in: pale yellow oil; commercially available.
Purification: distill at <1 mmHg.
Handling, Storage, and Precautions: material should be stored under a dry atmosphere of Ar or N2 at 0 °C. Many carbodiimides are strong sensitizers, therefore 1,3-bis(2,2-dimethyl-1,3-dioxolan-4-ylmethyl)carbodiimide (BDDC) should be considered as such. Avoid all skin contact, and use proper personal protection equipment (gloves, goggles, lab coat, etc.). BDDC should only be used in a well-ventilated fume hood. BDDC is incompatible with strong acids, including aqueous acids. BDDC is flammable; avoid fire or sparks. Decomposes upon prolonged storage at room temperature and exposure to air and moisture.
Preparative Methods: BDDC can be purchased commercially or it can be easily made in the laboratory from 3-aminomethyl-2,2-dimethyl-1,3-dioxolane.1
BDDC performs peptide couplings, esterifications, and dehydrations similar to the well known carbodiimides dicyclohexylcarbodiimide (DCC), diisopropylcarbodiimide (DIC), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDC),2 but is designed to be easily removed from reaction mixtures with dilute acidic washes (
BDDC is an excellent reagent for the coupling of amino acids to form peptide bonds (
Many methods are known for esterifying carboxylic acids.3 Strongly acidic or basic methods dominate these methods. One essentially neutral method is to employ an isourea (
The resulting isoureas convert carboxylic acids cleanly to the corresponding esters without the use of harshly acidic or basic reagents (
This is desirable when sensitive functional groups are present in the molecule and racemization must be avoided. The isourea reacts at the oxygen center, and not the carbonyl, so a-racemization cannot occur.
Carbodiimides are also employed as general dehydrating agents.2 BDDC was used to dehydrate benzyl 3-hydroxybutanoate to benzyl crotonate in 83% yield.
Bristol-Myers Squibb, New Brunswick, New Jersey, USA