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Can I read Practical One-Pot Synthesis of N -( tert -Butoxycarbonyl)sulfamide from Chlorosulfonyl Isocyanate via N -( tert -Butoxycarbonyl)aminosulfonylpyridinium Salt on EtoBox?
Practical One-Pot Synthesis of N -( tert -Butoxycarbonyl)sulfamide from Chlorosulfonyl Isocyanate via N -( tert -Butoxycarbonyl)aminosulfonylpyridinium Salt by Toshiaki Masui; Mikio Kabaki; Hideaki Watanabe; Tatsuya Kobayashi; Yoshiyuki Masui is a Chemistry article available to read on EtoBox.
What is Practical One-Pot Synthesis of N -( tert -Butoxycarbonyl)sulfamide from Chlorosulfonyl Isocyanate via N -( tert -Butoxycarbonyl)aminosulfonylpyridinium Salt about?
An efficient and practical process for the one-pot synthesis of N-(tert-butoxycarbonyl)sulfamide (4), a raw material for the aminosulfamoyl-containing side chain 3 of a novel carbapenem antibiotic doripenem hydrate (S-4661: 1), is described. In the previous process, chlorosulfonyl isocyanate was converted to N-(tert-butoxycarbonyl)aminosulfonyl chloride (7), an extremely unstable intermediate against moisture, which afforded the target compound 4 using liquid ammonia at cryogenic temperatures in 90% isolated yield. The use of liquid ammonia required cryogenic reaction temperatures because of heat generated from the highly exothermic reaction and the low boiling point of ammonia. In the improved process, the deactivation of the sulfonyl chloride 7 with pyridine at 0 °C afforded water-resistant N-(tert-butoxycarbonyl)aminosulfonylpyridinium salt (8) which was converted in situ to the target compound 4 in the presence of water at 0 °C in 90-96% isolated yields. Aqueous ammonia can be used, and no cryogenic temperatures are necessary for this new one-pot process.
Who reads Practical One-Pot Synthesis of N -( tert -Butoxycarbonyl)sulfamide from Chlorosulfonyl Isocyanate via N -( tert -Butoxycarbonyl)aminosulfonylpyridinium Salt?
It is typically read by researchers, students, and practitioners in Chemistry.
- Author
- Toshiaki Masui; Mikio Kabaki; Hideaki Watanabe; Tatsuya Kobayashi; Yoshiyuki Masui
- Publisher
- American Chemical Society (ACS)
- Published
- 2004
- Language
- EN
- Field
- Chemistry (Physical Sciences)