Trityl chloride → HCID 23138562, compound

HRID 1171717Notes

Reaction equation

HRID 1171717 reaction equation
C(N(CC)CC)C.Cl[C:9]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.FC(F)(F)C(O)=O.[C:35]([S:38][CH:39]1[CH2:44][CH2:43][NH:42][CH2:41]/[C:40]/1=[CH:45]\[C:46]1[CH:50]=[CH:49][N:48]([CH2:51][CH2:52][C:53]([O:55][CH2:56][CH3:57])=[O:54])[N:47]=1)(=[O:37])[CH3:36]>CN(C)C=O.C(OCC)(=O)C.C(OCC)C>[C:35]([S:38][CH:39]1[CH2:44][CH2:43][N:42]([C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:41]/[C:40]/1=[CH:45]\[C:46]1[CH:50]=[CH:49][N:48]([CH2:51][CH2:52][C:53]([O:55][CH2:56][CH3:57])=[O:54])[N:47]=1)(=[O:37])[CH3:36]

Participants

7

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 23138503HCID 23138503, compound

Product 1

HCID 23138562HCID 23138562, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (16.2 ml) and chlorotriphenylmethane (10.91 g) were added to a solution of the racemic (E)-4-(acetylsulfanyl)-3-({1-[2-(ethoxycarbonyl)ethyl]-1H-pyrazol-3-yl}methylidene)piperidine hydrogen trifluoroacetate (Example 111-(c), 22.09 g) in N,N-dimethylformamide (150 ml) at 0° C. After the mixture was stirred at room temperature for 2 hours, it was diluted with a mixed solvent of ethyl acetate and diethyl ether (2:1), and the solution was washed successively with water and a saturated aqueous sodium chloride solution. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (eluent: hexane/ethyl acetate=95/5˜30/70) to give racemic (E)-4-(acetylsulfanyl)-3-({1-[2-(ethoxycarbonyl)ethyl]-1H-pyrazol-3-yl}methylidene)-1-(triphenylmethyl)piperidine (19.40 g, yield: 86%).

Workup

  1. washthe solution was washed successively with water
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (eluent: hexane/ethyl acetate=95/5˜30/70)

Sources & evidence

ORD record
ord-ed543c8855d84e7c8932d441473ddbad
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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