Highly reactive, water soluble carbodiimides, intermediates and

Details Highly reactive, water soluble carbodiimides, intermediates and Highly reactive, water soluble carbodiimides, intermediates and

1994-11-28

1997-02-11

Trinh, Ba K.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D31726, C07D31728

Patent

active

056022646

ABSTRACT:
Novel water soluble carbodiimides, and intermediates or derivatives thereof, such as isoureas or isothioureas, are described. A particularly preferred embodiment is bis[4-(2,2-dimethyl-1,3-dioxolyl)methyl] carbodiimide (BDDC), which can be synthesized efficiently from 1,2-isopropylideneglycerol (solketal). The isoureas are effective esterifying agents. The corresponding N-protected amino acid tert-butyl, benzyl, isopropyl, ethyl, and methyl esters can be synthesized in high yield under neutral conditions, with no urea residue after simply washing with aqueous acid. Amino acid couplings utilizing carbodiimide embodiments give peptides in good yield, free of carbodiimide by-products, after washing with dilute acid, while racemization-free peptides are also obtained.

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