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- The newly formed methylenic carbon appears at δ 68.89 ppm (assigned using HETCOR) and not at - δ 43 ppm confirms the structure of 2b. The methylenic carbon of N-(tert-butoxycarbonyl)-glycine tert-butyl ester in CDCI3 resonates at δ 43.03 ppm
- Lower reaction temperatures, −78 or −40°, resulted in a lower yield of 2b, 41% and 42% respectively, while 4b was produced in higher yields, 19% and 22% respectively. Room temperature deprotonation and alkylation afforded only 21 % of 2b, 14% of 4b and many other unidentified by-products. Changing the counterion to either sodium or lithium drastically reduced the yield of 2b, 21% and 17%, respectively. No other reaction solvents were investigated, however, attempted alkylation of the intermediate alkoxide with the lithium or potassium salt of bromoacetic acid only afforded the desired acid in <10% yield
- An oxazolidinone is obtained as a result of an internal displacement of benzyloxy group followed by N-alkylation with tert-butyl bromoacetate
- Leabeau , L. , Oudet , P. and Mioskowski , C. 1991 . Helv. Chim. Acta , 74