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

• Published in: Tetrahedron letters 2002-11, Vol.43 (46), p.8327-8330
• Main Authors: Rastogi, S.K., Srivastava, G.K., Singh, S.K., Grover, R.K., Roy, R., Kundu, B.
• Format: Article
• Language: English
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/S0040-4039(02)02009-9

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. A versatile method for the solid phase synthesis of oxazolidin-2-ones has been 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 the 5-substituted oxazolidinone. Finally, additional diversity at position 3 was introduced by treating the 5-substituted oxazolidinone with alkyl halides in the presence of NaH to give the desired compounds in high yields and purities.