Sodium Chloride → HCID 86609429, compound

HRID 1171673Notes

Reaction equation

HRID 1171673 reaction equation
[CH3:1][O:2][C:3]([CH2:5][CH2:6][N:7]1[CH:11]=[C:10](/[CH:12]=[C:13]2\[CH2:14][N:15]([C:20]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:16][CH2:17][CH:18]\2O)[N:9]=[N:8]1)=[O:4].[C:39]([OH:42])(=[S:41])[CH3:40].C(OC(OCC(C)(C)C)N(C)C)C(C)(C)C.[Cl-].[Na+]>C1(C)C=CC=CC=1>[C:39]([S:41][CH:18]1[CH2:17][CH2:16][N:15]([C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:14]/[C:13]/1=[CH:12]\[C:10]1[N:9]=[N:8][N:7]([CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[CH:11]=1)(=[O:42])[CH3:40]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 786231,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamineHCID 23139017HCID 23139017, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 86609429HCID 86609429, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (E)-3-({1-[2-(methoxycarbonyl)ethyl]-1H-1,2,3-triazol-4-yl}methylidene)-1-(triphenylmethyl)piperidin-4-ol (13.15 g) in toluene (200 ml) were added thioacetic acid (3.7 ml) and N,N-dimethylformamide dineopentyl acetal (14.5 ml) at room temperature and the resulting mixture was stirred at the same temperature for 30 minutes. After aqueous sodium chloride solution was added, products were extracted with ethyl acetate and the extract was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate. After evaporation of the solvent under reduced pressure, the residue was purified by silica gel chromatography using ethyl acetate and hexane (1:1) as the eluent to afford a mixture (12.92 g) of (E)-4-(acetylsulfanyl)-3-({1-[2-(methoxycarbonyl)ethyl]-1H-1,2,3-triazol-4-yl}methylidene)-1-(triphenylmethyl)piperidine and 5-((acetylsulfanyl){1-[2-(methoxycarbonyl)ethyl]-1H-1,2,3-triazol-4-yl}methyl)-1-(triphenylmethyl)-1,2,3,6-tetrahydropyridine.

Workup

  1. extractionproducts were extracted with ethyl acetate
  2. washthe extract was washed with a saturated aqueous sodium chloride solution
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customAfter evaporation of the solvent under reduced pressure
  5. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-4a8abd6838b042b88edf5f58ebf9d008
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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