Method for reductive elimination of protecting groups

Details Method for reductive elimination of protecting groups Method for reductive elimination of protecting groups

1980-09-17

1986-01-14

Phillips, Delbert R.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

C07C10352

Patent

active

045644713

ABSTRACT:
The invention provides a novel and efficient method for the elimination of protecting groups, e.g. benzyloxycarbonyl group, from a protected amino acid, peptide or derivative thereof having at least one functional group protected by a protecting group, e.g. a lower alkyl ester of N-benzyloxycarbonyl-.alpha.-L-aspartyl-L-phenylalanine by catalytic hydrogen reduction to produce free amino acid, peptide or derivative thereof. In contrast to the conventional procedures in which the reaction is carried out in a solvent dissolving both the starting compound and the product compound or a solvent dissolving the starting compound but not dissolving the product compound, the inventive method utilizes a binary two-phase reaction medium composed of water and an organic solvent not freely miscible with water such as toluene. The reaction takes place in the organic phase containing the starting compound dissolved and the catalyst dispersed therein whereas the reaction product which is water-soluble is smoothly and successively transferred into the aqueous phase so that advantages are obtained in the unexpectedly high yield of the product as well as in the easiness of handling the reaction mixture after completion of the reaction.

REFERENCES:
patent: 3798204 (1974-03-01), Nakajima et al.
patent: 3853835 (1974-12-01), Mazur et al.
patent: 3972860 (1976-08-01), Moriarty et al.
patent: 4017472 (1977-04-01), Farkas et al.
Schroder et al., The Peptides, vol. I, pp. 26, 27, 1965.
H. T. Clarke et al., "A Handbook of Organic Analysis", (1975), p. 68.
Clarke et al., A Handbook of Organic Analysis, Fifth Edition, Edward Arnold (1968), pp. 65-67.

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