Pyridine → HCID 131728315, compound

HRID 507794Notes

Reaction equation

HRID 507794 reaction equation
[N:1]1C=C[CH:4]=[CH:3][CH:2]=1.[CH:7]([SiH:10]([CH:26]([CH3:28])[CH3:27])[C:11]1[CH:25]=[CH:24][C:14]([C:15]([NH:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[O:16])=[CH:13][CH:12]=1)([CH3:9])[CH3:8].C(CCO)#N.C(N(CC)CC)C>C(Cl)(Cl)Cl.O>[C:2]([CH2:3][CH2:4][O:22][C:21](=[O:23])[CH2:20][CH2:19][CH2:18][NH:17][C:15](=[O:16])[C:14]1[CH:13]=[CH:12][C:11]([SiH:10]([CH:7]([CH3:9])[CH3:8])[CH:26]([CH3:28])[CH3:27])=[CH:25][CH:24]=1)#[N:1]

Participants

7

Reactant 4

HCID 1049PyridineHCID 8011HydracrylonitrileHCID 8471TriethylamineHCID 123537105HCID 123537105, compound

Product 1

HCID 131728315HCID 131728315, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A condensing agent of N,N-bis (2-oxo-3-oxazolidinyl)-phosphnic acid chloride BOP-Cl (1.5 g, 6.1 mmol) was added to pyridine solution (20 mL) dissolving 4-[4-(diisopropylsilanyl)benzoylamino]butanoic acid (3) (1.3 g, 4.1 mmol), 2-cyanoethanol (548 μL, 8.1 mmol) and triethylamine (828 μL, 6.1 mmol). The resulting mixture was stirred for 3 hours at a room temperature and mixed with water (5 mL). Five minutes later, it was diluted with chloroform (200 mL) and extracted three times with 5 wt % aqueous solution (150 ml) of sodium hydrogen carbonate. An organic layer was collected and dehydrated with anhydrous sodium sulfate and filtered so that the resulting solvent was distilled out under a reduced pressure. The resulting crude product was then purified by silica gel column chromatography. After eluted with chloroform having 0-3% methanol gradient, the solvent was distilled out to give a desired product (1.2 g, 79%). Its NMR data are as follows:

Workup

  1. extractionextracted three times with 5 wt % aqueous solution (150 ml) of sodium hydrogen carbonate
  2. customAn organic layer was collected
  3. filtrationfiltered so that the resulting solvent
  4. distillationwas distilled out under a reduced pressure
  5. customThe resulting crude product was then purified by silica gel column chromatography
  6. washAfter eluted with chloroform having 0-3% methanol gradient
  7. distillationthe solvent was distilled out

Sources & evidence

ORD record
ord-8ac339ab8e6645ce97d7815bee8adfc4
Source dataset
uspto-grants-2010_08
Patent number
US07786296B2

Reaction notes

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