Water → HCID 86609412, compound

HRID 1171643Notes

Reaction equation

HRID 1171643 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1/[CH:13]=[C:14]1\[CH2:15][N:16]([C:21]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:17][CH2:18][CH:19]\1O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:40]([OH:43])(=[S:42])[CH3:41].C(OC(OCC(C)(C)C)N(C)C)C(C)(C)C.O>C1(C)C=CC=CC=1>[C:40]([S:42][CH:19]1[CH2:18][CH2:17][N:16]([C:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:15]/[C:14]/1=[CH:13]\[C:9]1[N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH:12]=[CH:11][N:10]=1)(=[O:43])[CH3:41]

Participants

6

Reactant 4

HCID 962WaterHCID 786231,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamineHCID 23139136HCID 23139136, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 86609412HCID 86609412, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (E)-3-{[1-(t-butoxycarbonyl)-1H-imidazol-2-yl]methylidene}-1-(triphenylmethyl)piperidin-4-ol (2.45 g) in toluene (100 ml) were added successively thioacetic acid (0.60 ml) and N,N-dimethylformamide dineopentyl acetal (2.36 ml) under ice-cooling, and the resulting mixture was stirred at room temperature 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 in vacuo, and the residue was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate, hexane and dichloromethane (1:5:1) as the eluent to afford the title compound (0.72 g, yield: 26%) as a colourless amorphous solid.

Workup

  1. temperaturecooling
  2. stirringAfter stirring
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium chloride solution
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-81b5e913fc314669b204ffcce390e500
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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