Sodium hydride → HCID 11268919, compound

HRID 2247059Notes

Reaction equation

HRID 2247059 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[O:9]1[C:11]2([CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH2:27][C@@H:26]([CH2:28][NH:29][C:30](=[O:32])[CH3:31])[O:25][C:24]4=[O:33])=[CH:19][C:18]=3[F:34])[CH2:13][CH2:12]2)[CH2:10]1>CS(C)=O>[O:9]1[C:11]2([CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH2:27][C@H:26]([CH2:28][NH:29][C:30](=[O:32])[CH3:31])[O:25][C:24]4=[O:33])=[CH:19][C:18]=3[F:34])[CH2:13][CH2:12]2)[CH2:10][CH2:4]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 86599015HCID 86599015, compound

Product 1

HCID 11268919HCID 11268919, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 60% sodium hydride (6.0 mmol), trimethyloxo sulfonium iodide (6.1 mmol) was stirred for 30 minutes and (R)-N-{3-[4-(1-oxa-6-aza-spiro[2.5]oct-6-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (4.80 mmol) in DMSO (20 ml) was stirred for 75 hour at the room temperature. The reaction mixture was poured on ice water and extracted with ethyl acetate. The organic layer was dried and concentrated in vacuum to provide crude compound. The crude compound was purified over silica gel column to provide title compound in 20% yield.

Workup

  1. additionThe reaction mixture was poured on ice water
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was dried
  4. concentrationconcentrated in vacuum
  5. customto provide crude compound
  6. customThe crude compound was purified over silica gel column

Sources & evidence

ORD record
ord-638290f165be4afbab778dc21c1c8c8f
Source dataset
uspto-grants-2010_03
Patent number
US07687627B2

Reaction notes

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