Water → HCID 23138681, compound

HRID 1171678Notes

Reaction equation

HRID 1171678 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][CH2:7][CH2:8][N:9]1[CH:13]=[C:12](/[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)[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].O>CN(C)C=O.C(OCC)(=O)C>[C:57]([S:59][CH:20]1[CH2:19][CH2:18][N:17]([C:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:16]/[C:15]/1=[CH:14]\[C:12]1[N:11]=[N:10][N:9]([CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:13]=1)(=[O:60])[CH3:58]

Participants

7

Reactant 4

HCID 962WaterHCID 786231,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamineHCID 23138695HCID 23138695, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 23138681HCID 23138681, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (E)-3-({1-[3-(ethoxycarbonyl)propyl]-1H-1,2,3-triazol-4-yl}methylidene)-1-(triphenylmethyl)piperidin-4-ol (13.7 g) in N,N-dimethylformamide (50 ml) were added N,N-dimethylformamide dineopentyl acetal (14.2 ml) and thioacetic acid (3.4 ml) with stirring at room temperature. The resulting mixture was stirred at room temperature for 0.5 hours and then water and ethyl acetate were added to separate the layers. After the organic layer was washed with a saturated aqueous sodium chloride solution, it was dried over anhydrous magnesium sulfate. After evaporation of the under reduced pressure, the residue was purified by silica gel chromatography using ethyl acetate, hexane, and dichloromethane (2:1:1 to 1:1:1) as the eluent to afford an approximately 1:2 mixture (12.8 g) of (E)-4-(acetylsulfanyl)-3-({1-[3-(ethoxycarbonyl)propyl]-1H-1,2,3-triazol-4-yl}methylidene)-1-(triphenylmethyl)piperidine and 5-((acetylsulfanyl){1-[3-(ethoxycarbonyl)propyl]-1H-1,2,3-triazol-4-yl}methyl)-1-(triphenylmethyl)-1,2,3-tetrahydropyridine. Furthermore, this mixture contained a small amount of (Z)-4-(acetylsulfanyl)-3-({1-[3-(ethoxycarbonyl)propyl]-1H-1,2,3-triazol-4-yl}methylidene)-1-(triphenylmethyl)piperidine.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 0.5 hours
  2. customto separate the layers
  3. washAfter the organic layer was washed with a saturated aqueous sodium chloride solution, it
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. customAfter evaporation of the under reduced pressure
  6. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-6e5b2a55431d4279b967fe0da8744047
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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