Synthesis of carbon-14 labelled spiro-piperidyl-rifamycins (LM 118) and rifabutin (LM 427)
✍ Scribed by Erminia Fontana; Silvio Giarda; Sergio Vioglio; Gian Piero Vicario
- Publisher
- John Wiley and Sons
- Year
- 1987
- Tongue
- French
- Weight
- 330 KB
- Volume
- 24
- Category
- Article
- ISSN
- 0022-2135
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✦ Synopsis
Two syntheses of radiolabelled spiro-piperidyl-rifamycins are described. 1. A five steps synthesis (Scheme 1) was performed to give 4-deoxo-3 , 4-[ 2-spiro-(N-[ 14C Imathyl-4-piperidyl) ] -(1H) -imidazo-(2 , 5-dihydro) -rifamycin 6 ( [ 14C JIM 118) , in an overall radiochemical yield 0fN20%, 98% radiochemically pure and with a specific activity of 440 MBq/mmol (11.9 mCi/mmol)starting from [14C]plethyl iodide 1. 2. A three steps synthesis (Scheme 2)was performed to give I-deoxo-3 , 4-[ 2-spiro-(N-2-methyl[ 1-14C ]propane-4-piperidyl) ] -(1H) -imida-14 zo-(2,5-dihydro)-rifamycin S ( [ C] rifabutin) in an overall radiochemical yield of438%, 972 radiochemically pure with a specific activity of 1.27 GBq/mol (34.32 mci/mmol). 1-(2-Hethyl [ l-14C]propanoyl) -piperazin-4-one ethylene ketal was employed as starting material.