Triethylamine → HCID 53883525, compound

HRID 1108595Notes

Reaction equation

HRID 1108595 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

Conditions

Temperature
0 °C

Procedure

(5R)-3-(3-Fluoro-4-{4-(2-fluoroethyl)-3-oxopiperazin-1-yl}phenyl)-5-hydroxymethyl-oxazolidin-2-one (0.8 g) was dissolved in pyridine (15 ml), and the mixture cooled to 0° C. Triethylamine (0.38 ml) and methanesulfonyl chloride (0.19 ml) were added to the mixture, and stirring continued at ambient temperature for 2 hours. Solvent was evaporated and the residue dissolved in dichloromethane, washed with water, brine, dried (MgSO4), and evaporated. The resulting residue was titurated with diethyl ether to give (5R)-3-(3-fluoro-4-{4-(2-fluoroethyl)-3-oxopiperazine-1-yl}phenyl)-5-(methanesulfonyloxymethyl)-oxazolidin-2-one (0.76 g) which was used without further purification.

Workup

  1. customSolvent was evaporated
  2. dissolutionthe residue dissolved in dichloromethane
  3. washwashed with water, brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-a754438475c84ee7b81c6353d7a9e82e
Source dataset
uspto-grants-2000_05
Patent number
US06069145

Reaction notes

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