Sodium Chloride → HCID 23138538, compound

HRID 1171675Notes

Reaction equation

HRID 1171675 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][CH2:7][CH2:8][N:9]1[C:13](/[CH:14]=[C:15]2\[CH2:16][N:17]([C:22]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:18][CH2:19][CH:20]\2O)=[CH:12][N:11]=[N:10]1)=[O:5])[CH3:2].C(OC(OCC(C)(C)C)N(C)C)C(C)(C)C.[C:57]([OH:60])(=[S:59])[CH3:58].[Cl-].[Na+]>CN(C)C=O>[C:57]([S:59][CH:20]1[CH2:19][CH2:18][N:17]([C:22]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:16]/[C:15]/1=[CH:14]\[C:13]1[N:9]([CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[N:10]=[N:11][CH:12]=1)(=[O:60])[CH3:58]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 786231,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamine4×HCID 23139059HCID 23139059, compoundHCID 178418634HCID 178418634, compound4×

Product 1

HCID 23138538HCID 23138538, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (E)-3-({1-[3-(ethoxycarbonyl)propyl]-1H-1,2,3-triazol-5-yl}methylidene)-1-(triphenylmethyl)piperidin-4-ol (14.34 g) in N,N-dimethylformamide (100 ml) was added N,N-dimethylformamide dineopentyl acetal (14.90 ml). Then thioacetic acid (3.58 ml) was added to the reaction mixture under ice-cooling. The resulting mixture was stirred at room temperature for 30 minutes and then N,N-dimethylformamide dineopentyl acetal (14.90 ml) and additional thioacetic acid (3.58 ml) were supplemented, and the resulting mixture was stirred for one hour. Further N,N-dimethylformamide dineopentyl acetal (14.90 ml) and thioacetic acid (3.58 ml) were added, and the resulting mixture was stirred for 30 minutes. Still further N,N-dimethylformamide dineopentyl acetal (14.90 ml) and thioacetic acid (3.58 ml) were added, and the resulting mixture was stirred for 30 minutes. Then aqueous sodium chloride solution was added to the reaction mixture, and the product was 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 repeatedly purified for three times by silica gel chromatography using ethyl acetate and hexane (1:1 or 2:1) as the eluent to afford the less polar isomer title compound (7.45 g, yield: 47%), as a yellow foam and the more polar isomer 5-((acetylsulfanyl){1-[3-(ethoxycarbonyl)propyl]-1H-1,2,3-triazol-5-yl}methyl)-1-(triphenylmethyl)-1,2,3,6-tetrahydropyridine (5.58 g, yield: 35%) as an orange-coloured foam, respectively.

Workup

  1. temperaturecooling
  2. stirringthe resulting mixture was stirred for one hour
  3. stirringthe resulting mixture was stirred for 30 minutes
  4. stirringthe resulting mixture was stirred for 30 minutes
  5. extractionthe product was extracted with ethyl acetate
  6. washThe extract was washed with a saturated aqueous sodium chloride solution
  7. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  8. customAfter evaporation of the solvent under reduced pressure
  9. customthe residue was repeatedly purified for three times by silica gel chromatography

Sources & evidence

ORD record
ord-eabf8b4fe1bc4abba120073b8bd025a6
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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