The use of the acetonide derivative in the preparation of D-threo-chloramphenicol-1-3H and its nitroso derivative

✍ Scribed by J. Richard Heys

• Publisher: John Wiley and Sons
• Year: 1981
• Tongue: French
• Weight: 432 KB
• Volume: 18
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2580181206

✦ Synopsis

Abstract

An efficient synthesis of millimolar quantities of high specific activity D‐threo‐chloramphenicol‐1‐^3^H is described. The key step is the chromatographic separation of the compound from its 1‐epimer, produced in the Ca(B^3^H~4~)~2~ reduction of chloramphenicol ketone (D‐α‐dichloroacetyl‐amino‐β‐hydroxy‐p‐nitropropiophenone), by use of the acetonide derivative. Stereochemical aspects of the N‐bromosuccinimide oxidation of chloramphenicol to chloramphenicol ketone have been investigated, and the previously reported [1] specific rotation of chloramphenicol ketone has been corrected. The synthesis of nitrosochloramphenicol‐1‐^3^H is described.