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- For bulk drug production no more than 10 ppm of any heavy metal may be present in the final product
- Although an internal temperature greater than 30°C appeared necessary for complete conversion, temperatures above 40°C during oxidant addition or the use of more than 0.5 equivalents of NaBrO3 gave lower yields, presumably due to product decomposition
- Subsequent crystallization of later intermediates further reduced the residual ruthenium to less than 1 ppm
- The reaction proceeded in the absence of TFAA, but complete conversion required longer reaction times
- NMR analysis of the crude products indicated that N-sulfonylation was a possible byproduct. Based upon 13C NMR (R. A. Reamer) the amide tautomer depicted predominates which may explain this result
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- PBr3 and PBr5 were also examined but failed to give the desired bromide
- Attempted hydrolysis of the bisamide 11 to the desired acid was not successful