Triethylamine → (5R)-3-(3-fluoro-4-{4-methyl-3-oxopiperazin-1-yl}phenyl)-5-(methanesulfonyloxymethyl)oxazolidin-2-one
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:16]2[CH2:20][C@H:19]([CH2:21][OH:22])[O:18][C:17]2=[O:23])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([CH3:14])[C:10](=[O:15])[CH2:9]1.C(N(CC)CC)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([N:16]2[CH2:20][C@H:19]([CH2:21][O:22][S:32]([CH3:31])(=[O:34])=[O:33])[O:18][C:17]2=[O:23])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([CH3:14])[C:10](=[O:15])[CH2:9]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
(5R)-3-(3-Fluoro-4-{4-methyl-3-oxopiperazin-1-yl}phenyl)-5-hydroxymethyloxazolidin-2-one (900 mg) was dissolved in pyridine (20 ml), and cooled to 0° C. Triethylamine (0.5 ml) and methanesulfonyl chloride (0.24 ml) were added, and stirring continued at 5° C. for 2 hours. Solvent was evaporated, and the residue chromatographed on silica, using as eluant a gradient increasing in polarity from 0 to 3% methanol in dichloromethane. Relevant fractions were combined and evaporated to give (5R)-3-(3-fluoro-4-{4-methyl-3-oxopiperazin-1-yl}phenyl)-5-(methanesulfonyloxymethyl)oxazolidin-2-one (990 mg).
Workup
- customSolvent was evaporated
- customthe residue chromatographed on silica
- temperaturea gradient increasing in polarity from 0 to 3% methanol in dichloromethane
- customevaporated
Sources & evidence
- ORD record
- ord-2758d53c4ebc4586a2dfef40c4aa7f8d
- Source dataset
- uspto-grants-2000_05
- Patent number
- US06069145
Reaction notes
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