Triethylamine → (5R)-3-(3-fluoro-4-{4-ethyl-3-oxopiperazin-1-yl}phenyl)-5-(methanesulfonyloxymethyl)-oxazolidin-2-one

HRID 1108581Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([N:17]2[CH2:21][C@H:20]([CH2:22][OH:23])[O:19][C:18]2=[O:24])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH3:15])[C:10](=[O:16])[CH2:9]1.C(N(CC)CC)C.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([N:17]2[CH2:21][C@H:20]([CH2:22][O:23][S:33]([CH3:32])(=[O:35])=[O:34])[O:19][C:18]2=[O:24])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH3:15])[C:10](=[O:16])[CH2:9]1

Participants

Conditions

Temperature: 0 °C

Procedure

(5R)-3-(3-Fluoro-4-{4-ethyl-3-oxopiperazin-1-yl}phenyl)-5-hydroxymethyloxazolidin-2-one (830 mg) was dissolved in pyridine (20 ml), and cooled to 0° C. Triethylamine (0.41 ml) and methanesulfonyl chloride (0.21 ml) were added, and stirring continued at ambient temperature for 2 hours. Solvent was evaporated and the residue dissolved in ethyl acetate. The resulting solution was washed with water, dried (MgSO4), and evaporated to give (5R)-3-(3-fluoro-4-{4-ethyl-3-oxopiperazin-1-yl}phenyl)-5-(methanesulfonyloxymethyl)-oxazolidin-2-one (1.0 g) which was used without further purification.

Workup

customSolvent was evaporated
dissolutionthe residue dissolved in ethyl acetate
washThe resulting solution was washed with water
dry with materialdried (MgSO4)
customevaporated

Sources & evidence

ORD record: ord-62861ec18e6843cd8150c093dbed1c34
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06069145

Reaction notes

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