Triethylamine → HCID 53883525, compound

HRID 1637164Notes

Reaction equation

HRID 1637164 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:18]2[CH2:22][C@H:21]([CH2:23][OH:24])[O:20][C:19]2=[O:25])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][F:16])[C:10](=[O:17])[CH2:9]1.C(N(CC)CC)C.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([N:18]2[CH2:22][C@H:21]([CH2:23][O:24][S:34]([CH3:33])(=[O:36])=[O:35])[O:20][C:19]2=[O:25])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][F:16])[C:10](=[O:17])[CH2:9]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 54327468HCID 54327468, compound

Product 1

HCID 53883525HCID 53883525, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(5R)-3-(3-Fluoro-4-[4-(2-fluoroethyl)-3-oxopiperazin-1-yl]phenyl)-5-hydroxymethyloxazolidin-2-one (0.8 g) is dissolved in pyridine (15 ml) and the mixture cooled to 0°. Triethylamine (0.38 ml) and methanesulfonyl chloride (0.19 ml) are added to the mixture, and stirring continued at 20-25° for 2 hours. The solvent is removed and the residue dissolved in dichloromethane, washed with water, saline, dried over magnesium sulfate and concentrated. The resulting residue is triturated with ether to give (5R)-3-(3-fluoro-4-[4-(2-fluoroethyl)-3-oxopiperazin-1-yl]phenyl)-5-(methanesulfonyloxymethyl)oxazolidin-2-one (0.76 g) which is used without further purification.

Workup

  1. temperaturethe mixture cooled to 0°
  2. customThe solvent is removed
  3. dissolutionthe residue dissolved in dichloromethane
  4. washwashed with water, saline
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe resulting residue is triturated with ether

Sources & evidence

ORD record
ord-70b01e5b98f74206aafbd2bc70ea7754
Source dataset
uspto-grants-2000_03
Patent number
US06040306

Reaction notes

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