.alpha.-chlorinated carbonates, their method of manufacture and

Details .alpha.-chlorinated carbonates, their method of manufacture and .alpha.-chlorinated carbonates, their method of manufacture and

1988-06-06

1990-10-02

Brust, Joseph Paul

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

Organic compounds

Extracting solid from solution

546 14, 546226, 548406, 548528, 548533, 556420, 558392, 558441, 560 13, 560 16, 560 17, 560 24, 560 29, 560 30, 560 31, 560 32, 560132, 560136, 560148, 560157, C07D49948, C07D20708

Patent

active

049608819

ABSTRACT:
The invention relates to carbonates of formula: ##STR1## in which X is a fluorine, chlorine or bromine atom and R.sup.1 is different from the ##STR2## group and represents: a substituted or non-substituted, saturated or unsaturated, aliphatic, araliphatic, primary, secondary, tertiary or cycloaliphatic radical. These .alpha.-chlorinated carbonates are prepared by the action of a compound of formula R.sup.1 OH on a chloroformate of formula: ##STR3## in a solvent medium in the presence of an acid scavenger which is added after the two preceding compounds. They are used to block the amine function of amino acids. The .alpha.-chlorinated carbonate and amino acid are reacted in a solvent medium at a temperature of -5.degree. to 100.degree. C. in the presence of an acid scavenger. Blocked amines are very useful in peptide synthesis.

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C.A. 51:7148f (1957), Hales et al.
McOmie, "Protective Groups in Organic Chemistry", (1973), p. 58: Plenum Press, London & N.Y.
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Broadbent et al.--Polypeptides, Part V..sup.1. The Use of t-Butyl 2,4,5-Trichlorophenyl Carbonate in the Synthesis of N-t-Butoxycarbonyl Amino-Acids and their 2,4,5-Trichlorophenyl Esters J. Chem. Soc. (C) (1967), pp. 2632-2636.
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