Sodium Chloride → HCID 23139002, compound

HRID 1171668Notes

Reaction equation

HRID 1171668 reaction equation
[CH3:1][O:2][C:3]([CH2:5][CH2:6][N:7]1[C:11](/[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)=[CH:10][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:12]([C:11]1[N:7]([CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[N:8]=[N:9][CH:10]=1)[C:13]1[CH2:14][N:15]([C:20]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:16][CH2:17][CH:18]=1)(=[O:42])[CH3:40]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 786231,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamineHCID 23138758HCID 23138758, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 23139002HCID 23139002, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (E)-3-({1-[2-(methoxycarbonyl)ethyl]-1H-1,2,3-triazol-5-yl}methylidene)-1-(triphenylmethyl)piperidin-4-ol (13.22 g) in toluene (200 ml) were added thioacetic acid (3.7 ml) and N,N-dimethylformamide dineopentyl acetal (14.5 ml) with stirring at room temperature, and the resulting mixture was stirred at the same temperature for 2 hours. After addition of aqueous sodium chloride solution, products were extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium chloride solution and 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 a mixed solvent of ethyl acetate and hexane (2:1) as the eluent to afford 5-((acetylsulfanyl){1-[2-(methoxycarbonyl)ethyl]-1H-1,2,3-triazol-5-yl}methyl)-1-(triphenylmethyl)-1,2,3,6-tetrahydropyridine (8.17 mg, yield: 55%) as a pale yellow amorphous solid.

Workup

  1. stirringthe resulting mixture was stirred at the same temperature for 2 hours
  2. extractionwere extracted with ethyl acetate
  3. washThe extract was washed with a saturated aqueous sodium chloride solution
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. customAfter evaporation of the solvent under reduced pressure
  6. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-f3cdbfb3b58b4e18a7ff88e99c284deb
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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