Ammonium Chloride → HCID 11394556, compound

HRID 2247053Notes

Reaction equation

HRID 2247053 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-cyanomethylidenepiperidin-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-3bf499dfff4943ffb3334f7d7435d6d1
Source dataset
uspto-grants-2010_03
Patent number
US07687627B2

Reaction notes

Loading…