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Solid phase synthesis of 3,5-disubstituted oxazolidin-2-ones

✍ Scribed by S.K. Rastogi; G.K. Srivastava; S.K. Singh; R.K. Grover; R. Roy; B. Kundu

Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 140 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)02009-9

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✦ Synopsis

A versatile method for the solid phase synthesis of oxazolidin-2-ones is described. A resin bound phenolic group was treated with (±)-epichlorohydrin followed by opening of the epoxide ring with sodium azide. The resulting 1-azido-3-aryloxypropan-2-ol was treated with p-nitrophenylchloroformate and subsequent Staudinger's cyclization using PPh 3 yielded a 5-substituted oxazolidinone. Finally, additional diversity at position 3 was introduced by treating the 5-substituted oxazolidinone with an alkyl halide in the presence of NaH to give the desired compound in high yield and purity.

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