By Wilhelm Foerst (Eds.)
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Also W . Ried and H. J. Schmidt, German Patent 1,064,508 (1957); Chem. Abstr. 55, 15447 (1961). (117) W . Ried and A. Urschel, Chem. Ber. 9 1 , 2459 (1958). (118) W . Ried, H. J. Schmidt, and A. Urschel, Chem. Ber. 91, 2472 (1958). (119) D. Marshall and M . C. Whitting, J. Chem. Soc. p. 4082 (1956); see also E. L. Pippen and M . Nonaka, / . Org. Chem. 23, 1580 (1958). (120) A. Dornow and P. Ische, Angew. Chem. 67, 653 (1955); German Patent 953,879 (1955); Chem. Zentr. p. 5652 (1957). (120a) W .
42 ml of P C 1 and 20 ml of 3 pyridine. 3 gm of N - c a r b o b e n z o x y - L glutamic acid α - e t h y l ester and an additional 30 ml of pyridine. T h e mixture is heated on the boiling water bath for 3 hr. p. 114-116° (from ethyl acetate-petroleum ether). A n example of the use of the method in the synthesis of more c o m plicated oligopeptides is the preparation of glutathione (see a b o v e ) . S-Benzyl-L-cysteinylglycine ethyl ester was obtained b y the reaction of N - c a r b o b e n z o x y - S - b e n z y l - L - c y s t e i n e with the phosphorazo c o m p o u n d of glycine ethyl ester followed b y splitting off the protective This phosphorazo compound of group.
In order to obtain analytically pure phenylimino (phenylamino) phosphine, the compound must be handled in the absence of air or oxygen. N o direct proof has been advanced for the structure of I I (16). close genetic relations to c o m p o u n d I I I , whose chain The structure was proved through dipole measurement, make it seem reasonable that I I has the structure designated. T h e reactions of I I are best indicated through a cryptoionic m e c h anism: the polar Ρ - Ν " δ + bond is split in such a w a y that an electro δ negative reactant goes to the phosphorus atom, an electropositive to the nitrogen.