2-Fluoroethyl bromide → 5-(S)-Azidomethyl-3-[4'-(2''-fluoroethyl)thio-3'-fluorophenyl]oxazolidine-2-one
Reaction equation
[N:1]([CH2:4][C@H:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[C:13]([F:19])[CH:12]=2)[CH2:6]1)=[N+:2]=[N-:3].BrC[CH2:22][F:23].N(C[C@H]1OC(=O)N(C2C=CC(SC(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=C(F)C=2)C1)=[N+]=[N-]>>[N:1]([CH2:4][C@H:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([S:17][CH2:18][CH2:22][F:23])=[C:13]([F:19])[CH:12]=2)[CH2:6]1)=[N+:2]=[N-:3]Participants
4
Reactant 3
Product 1
Procedure
This compound was prepared analogously to the synthesis of 5-(S)-azidomethyl-3-[4′-methylthio-3′-fluorophenyl]oxazolidine-2-one from 1-bromo-2-fluoroethane (0.109 ml, 1.47 mmol) and 5-(S)-azidomethyl-3-[4′-triphenylmethylthio-3′-fluorophenyl]-oxazolidine-2-one (0.500 g, 0.979 mmol). Yield 0.280 g (91%). MS (m/z): [M+H]+=315.