The Journal of organic chemistry

Synthesis of O-methyl-L-serine and N. alpha.-tert-butyloxycarbonyl-O-methyl-L-serine

RS Hodges, RB Merrifield

Index: Hodges,S.; Merrifield,R.B. Journal of Organic Chemistry, 1974 , vol. 39, p. 1870 - 1872

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Citation Number: 13

Abstract

0-Methyl-L-serine and Ne-tert-butyloxycarbonyl-0-methyl-L-serine were synthesized from L- serine via the in-termediate No-phthaloyl-L-serine p-nitrobenzyl ester. The ether was made with diazomethane and protecting groups were removed by catalytic hydrogenolysis and hydrazinolysis. Optical purity of the 0-methyl-L-serine was established. The methyl ether function was stable to the conditions used for acid hydrolysis of peptide bonds and to the ...