Dichloromethane → HCID 86609440, compound

HRID 1171691Notes

Reaction equation

HRID 1171691 reaction equation
[CH3:1][O:2][C:3]([CH2:5][N:6]1[C:10](/[CH:11]=[C:12]2\[CH2:13][N:14]([C:19]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:15][CH2:16][CH:17]\2O)=[CH:9][N:8]=[N:7]1)=[O:4].ClCCl.[C:41]([OH:44])(=[S:43])[CH3:42].C(OC(OCC(C)(C)C)N(C)C)C(C)(C)C>O.C1(C)C=CC=CC=1>[C:41]([S:43][CH:17]1[CH2:16][CH2:15][N:14]([C:19]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:13]/[C:12]/1=[CH:11]\[C:10]1[N:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[N:7]=[N:8][CH:9]=1)(=[O:44])[CH3:42]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 786231,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamineHCID 23138890HCID 23138890, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 86609440HCID 86609440, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of (E)-3-{[1-(methoxycarbonylmethyl)-1H-1,2,3-triazol-5-yl]methylidene}-1-(triphenylmethyl)piperidin-4-ol (6.27 g) in a mixed solvent of dichloromethane (100 ml) and toluene (100 ml) were added thioacetic acid (3.62 ml) and N,N-dimethylformamide dineopentyl acetal (14.0 ml). After the mixture was stirred at room temperature for 1 hour, water was added thereto and products were extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. Concentration under reduced pressure followed by purification of the residue by silica gel chromatography using hexane, ethyl acetate, and dichloromethane (2:1:1) as an eluent afforded crude (E)-4-(acetylsulfanyl)-3-{[1-(methoxycarbonylmethyl)-1H-1,2,3-triazol-5-yl]methylidene}-1-(triphenylmethyl)piperidine (4.0 g).

Workup

  1. extractionproducts were extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationConcentration under reduced pressure
  5. customfollowed by purification of the residue by silica gel chromatography

Sources & evidence

ORD record
ord-27a196feb66c4ae58cdbcedaa815fe94
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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