m-Chloroperbenzoic acid → 5-(S)-Azidomethyl-3-[4'-(2''-fluoroethyl)sulfinyl-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]([CH3:19])=[O:18])=[C:13]([F:20])[CH:12]=2)[CH2:6]1)=[N+:2]=[N-:3].N(C[C@H]1OC(=O)N(C2C=CC(SC[CH2:39][F:40])=C(F)C=2)C1)=[N+]=[N-].ClC1C=C(C=CC=1)C(OO)=O>>[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]([CH2:19][CH2:39][F:40])=[O:18])=[C:13]([F:20])[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′-methylsulfinyl-3′-fluorophenyl]oxazolidine-2-one from 5-(S)-azidomethyl-3-[4′-(2″-fluoroethyl)thio-3′-fluorophenyl]oxazolidine-2-one (0.280 g, 0.891 mmol) and m-chloroperoxybenzoic acid (77%, 0.200 g, 0.891 mmol). Yield 0.280 g (95%). MS (m/z): [M+H]+=331.
Sources & evidence
- ORD record
- ord-c18251a09a244b259e72d2a601f7ffa1
- Source dataset
- uspto-grants-2004_06
- Patent number
- US06743811B2
Reaction notes
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