Sodium hydride → HCID 69363345, compound

HRID 723815Notes

Reaction equation

HRID 723815 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[N:4]1.[S:8]1[CH2:13][CH:12]=[C:11]([C:14]2[C:19]([F:20])=[CH:18][C:17]([N:21]3[CH2:25][C@H:24]([CH2:26]OS(C)(=O)=O)[O:23][C:22]3=[O:32])=[CH:16][C:15]=2[F:33])[CH2:10][CH2:9]1>CN(C)C=O.C(=O)([O-])O.[Na+]>[S:8]1[CH2:9][CH:10]=[C:11]([C:14]2[C:19]([F:20])=[CH:18][C:17]([N:21]3[CH2:25][C@H:24]([CH2:26][N:4]4[N:5]=[CH:6][CH:7]=[N:3]4)[O:23][C:22]3=[O:32])=[CH:16][C:15]=2[F:33])[CH2:12][CH2:13]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 10179421HCID 10179421, compoundHCID 178418936HCID 178418936, compound

Product 1

HCID 69363345HCID 69363345, compoundYield 69.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Sodium hydride (60% in oil, 148 mg, 3.7 mmol) was suspended in dry N,N-dimethylformamide (5 ml) and 1,2,3-triazole (0.26 g, 3.7 mmol) was added under nitrogen. It was stirred for 5 minutes at room temperature and methanesulfonic acid (5R)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3,5-difluorophenyl]-2-oxo-oxazolidin-5-ylmethyl ester (see Example 86; 1.0 g, 2.47 mmol) was added. It was heated to 75° C. for 3.5 hours, then cooled to room temperature, diluted with aqueous sodium hydrogencarbonate solution (5%, 100 ml) and extracted with ethylacetate (2×100 ml). The organic phase was washed with water (2×50 ml), brine (100 ml), dried over magnesium sulfate and the solvent was evaporated in vacuo. Chromatography on silica gel with a gradient of 10–50% ethylacetate in hexanes gave the title compound (0.65 g). MS (ESP): 379. (MH+) for C17H16F2N4O2S

Workup

  1. temperatureIt was heated to 75° C. for 3.5 hours
  2. temperaturecooled to room temperature
  3. extractionextracted with ethylacetate (2×100 ml)
  4. washThe organic phase was washed with water (2×50 ml), brine (100 ml)
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-c325db21d9814fc0b20c16ddc151bea1
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

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