Sodium hydride → HCID 11268919, compound

HRID 1026712Notes

Reaction equation

HRID 1026712 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-7283ee89cd1b493b8b8b8cae5b808684
Source dataset
uspto-grants-2014_05
Patent number
US08729269B2

Reaction notes

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