(5S)-5-(Aminomethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone

The synthesis of a BP-linker-linezolid (BP-L-dLD, L: -SC(S)N-) conjugate is exemplified in the synthesis scheme depicted in FIG. 14. This chemistry is also applicable to other other deacetyl- oxazolidinones, such as eperezolid, radezolid, ranbezolid, sutezolid, et al.The synthesis of a BP-linker-linezolid (BP-L-dLD, L: -NC(S)N-) conjugate is exemplified in the synthesis scheme depicted in FIG. 15. This chemistry is also applicable to other other deacetyl- oxazolidinones, such as eperezolid, radezolid, ranbezolid, sutezolid, et al.The synthesis of a BP-linker-linezolid (BP-L-dLD, L: -OC(S)N-) conjugate is exemplified in the synthesis scheme depicted in FIG. 12. This chemistry is also applicable to other other deacetyl- oxazolidinones, such as eperezolid, radezolid, ranbezolid, sutezolid, et al.The synthesis of a BP-linker-deacetyl-linezolid (BP-L-dLD, L: -OC(O)N-) conjugate is exemplified in the synthesis scheme depicted in FIG. 8. This chemistry is also applicable to other deacetyl- oxazolidinones, such as eperezolid, radezolid, ranbezolid, sutezolid, et al.The synthesis of a BP-linker-deacetyl-linezolid (BP-L-dLD, L: -NC(O)N-) conjugate is exemplified inthe synthesis scheme depicted in FIG. 10. This chemistry is also applicable to other deacetyl- oxazolidinones, such as eperezolid, radezolid, ranbezolid, sutezolid, et al.General procedure: To a 50-ml glass round-bottom flask was added sequentially the primary amine 2 (1.0 mmol; aliphatic, aromatic or heteroaromatic; as free naked amine or as HCl, MsOH, TsOH or tartrate salt), FSO2N3 solution (containing 1.0 mmol FSO2N3, approximately 200 mM in DMF/MTBE 1:1, v/v, approximately 5 ml, volume adjusted according to the concentration; prepared according to the above procedure and diluted with equal volume of DMF) and aqueous KHCO3 solution (3.0 M, 1.33 ml, containing 4.0 mmol KHCO3). The reaction mixture was stirred for 5 min at room temperature, while monitoring by LC-MS. After completion, EtOAc (40 ml) was added and the mixture was washed sequentially with brine (60 ml × 6), water (60 ml × 2) and brine (60 ml), dried over Na2SO4, concentrated by rotary evaporation and dried under vacuum to afford the azide product 3. For products containing acidic functional groups, this extraction process was modified with acidified aqueous phase (acidified with aqueous HCl). Detailed procedures and the various modifications, as well as the characterization data for each compound, can be found in Supplementary Information 1.

Molecular Weight:295.31
XLogP3:0.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:3
Exact Mass:295.13321961
Monoisotopic Mass:295.13321961
Topological Polar Surface Area:68
Heavy Atom Count:21
Complexity:379
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes