By Eberhard Schröder and Klaus Lübke (Auth.)
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Extra resources for Methods of Peptide Synthesis. The Peptides, Volume 1
Peptide syntheses with these derivatives, however, have been described in only a few instances using the acid chloride method. The benzylsulfonyl group, like the toluenesulfonyl group, can be removed with sodium in liquid ammonia. It can also be reduced with I. AMINO-PROTECTING GROUPS 20 Raney nickel. The reaction can be carried out at normal pressure and room temperature. The nickel salts formed are removed from the aqueous solution with hydrogen sulfide. Removal of this group by catalytic hydrogenation in the presence of platinum oxide has not been possible.
ACYL-TYPE PROTECTING GROUPS 15 Another disadvantage of the reduction with sodium in liquid am monia is the difficulty of isolating the peptide in pure form. A large amount of inorganic salts must be removed; these are in part formed during the reaction, and in part are the result of the required destruction of the excess of metallic sodium by the addition of ammonium salts, such as ammonium chloride (642), ammonium iodide (2247), or am monium acetate (1847), or of acetic acid (2247). It is therefore advantageous to remove the sodium by the direct addition of Dowex 50 (H + form) (1516; cf.
Very poorly soluble compounds may be hydrogenated in glacial acetic acid (2292) or in the form of a suspension in dimethylformamide. Mixtures of watersaturated phenol with 2 N hydrochloric acid and ethanol have also served as a reaction medium at temperatures of 45°C (334). Hydrogenations are sometimes carried out in conventional solvents at higher tem perature (1938, 2104, 2620, 2626, 2637) or under higher pressure (2019a, 2071, 2104). Peptide esters are obtained by hydrogenation in the presence of glacial acetic acid (774).