Ammonium Chloride → HCID 11394556, compound

HRID 1026706Notes

Reaction equation

HRID 1026706 reaction equation
[I-].C[S+](C)(C)=O.[CH3:7]C(C)([O-])C.[K+].[C:13]([CH:15]=[C:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH2:32][C@H:31]([CH2:33][NH:34][C:35](=[O:37])[CH3:36])[O:30][C:29]3=[O:38])=[CH:24][CH:23]=2)[CH2:18][CH2:17]1)#[N:14].[Cl-].[NH4+]>CS(C)=O>[C:13]([CH:15]1[C:16]2([CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][C:25]([N:28]4[CH2:32][C@H:31]([CH2:33][NH:34][C:35](=[O:37])[CH3:36])[O:30][C:29]4=[O:38])=[CH:24][CH:23]=3)[CH2:18][CH2:17]2)[CH2:7]1)#[N:14]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 23665647Potassium tert-butoxideHCID 24885422HCID 24885422, compound

Product 1

HCID 11394556HCID 11394556, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of trimethyloxosulphonium iodide (10 mol), potassium tert-butoxide (10 mol) and (S)—N-[3-{4-[4-cyanomethylidene piperidin-1-yl]-phenyl}-2-oxo-1,3-oxazolidin-5-ylmethyl]-acetamide (8 mmol, Example A) in 20 ml dimethylsulfoxide, was stirred overnight at room temperature. The reaction mixture was worked up with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phase was dried evaporated to dryness to afford a residue, which was purified by column chromatography over silica gel to give solid in 47% yield.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phase was dried
  3. customevaporated to dryness
  4. customto afford a residue, which
  5. customwas purified by column chromatography over silica gel
  6. customto give solid in 47% yield

Sources & evidence

ORD record
ord-ee76731c04f74c498acc0b7db1bd5935
Source dataset
uspto-grants-2014_05
Patent number
US08729269B2

Reaction notes

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