9 research outputs found
Nitrosation of 4-amino-1-phenacyl-1,2,4-triazolium bromides and ?-(1,2,4-triazol-1-yl)acetophenones
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Practical Asymmetric Synthesis of an Edivoxetine·HCl Intermediate via an Efficient Diazotization Process
No full textA convergent
synthesis of (<i>S</i>)-(4-benzylmorpholin-2-yl)(morpholino)methanone
methanesulfonate (<b>1</b>), a key regulatory starting material
for edivoxetine·HCl, was developed at Eli Lilly & Company.
This novel synthesis utilizes d-serine as the source of chirality,
which is preserved throughout the synthesis. Key features include
the development of a scalable diazotization process to produce (<i>S</i>)-epoxy acid <b>7</b>, which was optimized to improve
the process safety profile. The final (<i>S</i>)-morpholino
acid intermediate <b>11</b> was converted to the title compound
using T3P with >99.9% purity in 75% yield. Life cycle analysis
of
the new route revealed a 69% reduction in global warming potential
(GWP) for solvent usage relative to the prior route of manufacture
Breast cancer cell-derived fibroblast growth factors enhance osteoclast activity and contribute to the formation of metastatic lesions
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