Triethylamine → HCID 86609408, compound

HRID 1171641Notes

Reaction equation

HRID 1171641 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]=[CH:11][C:10](/[CH:13]=[C:14]2\[CH2:15][N:16]([C:21]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:17][CH2:18][CH:19]\2O)=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CS(Cl)(=O)=O.C(N(CC)CC)C.[C:52]([O-:55])(=[S:54])[CH3:53].[K+]>ClCCl.O>[C:52]([S:54][CH:19]1[CH2:18][CH2:17][N:16]([C:21]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:15]/[C:14]/1=[CH:13]\[C:10]1[CH:11]=[CH:12][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[N:9]=1)(=[O:55])[CH3:53]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 23139301HCID 23139301, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 86609408HCID 86609408, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (E)-3-{[1-(t-butoxycarbonyl)-1H-pyrazol-3-yl]methylidene}-1-(triphenylmethyl)piperidin-4-ol (15.0 g) in dichloromethane (300 ml) were added successively methanesulfonyl chloride (2.5 ml) and triethylamine (4.5 ml) under ice-cooling, and the resulting mixture was stirred at room temperature for 1 hour and then evaporated in vacuo. Subsequently, to a solution of the residue thus obtained in dimethyl sulfoxide (200 ml) was added potassium thioacetate (16.5 g) at room temperature, and the resulting mixture was stirred at 50° C. for 30 minutes. After stirring, water was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was removed, and the residue was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate, hexane and dichloromethane (1:8:1) as the eluent to afford (E)-4-(acetylsulfanyl)-3-{[1-(t-butoxycarbonyl)-1H-pyrazol-3-yl]methylidene}-1-(triphenylmethyl) piperidine (including impurities) as a yellow amorphous solid.

Workup

  1. temperaturecooling
  2. customevaporated in vacuo
  3. customSubsequently, to a solution of the residue thus obtained in dimethyl sulfoxide (200 ml)
  4. stirringthe resulting mixture was stirred at 50° C. for 30 minutes
  5. stirringAfter stirring
  6. extractionthe resulting mixture was extracted with ethyl acetate
  7. washThe extract was washed with saturated aqueous sodium chloride solution
  8. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  9. customThe solvent was removed
  10. customthe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-1729bd3dae8043e99679d8133ece80af
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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