Dichloromethane → HCID 59424141, compound

HRID 501453Notes

Reaction equation

HRID 501453 reaction equation
F[B-](F)(F)F.[CH3:6][O+](C)C.ClCCl.[Si:13]([O:30][CH2:31][C:32]1[N:33]=[C:34]([N:44]2[CH2:49][CH2:48][N:47]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[CH2:46][CH2:45]2)[N:35]([CH2:40][C:41]#[C:42][CH3:43])[C:36]=1[C:37](=[S:39])[NH2:38])([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(OCC)(=O)C>[Si:13]([O:30][CH2:31][C:32]1[N:33]=[C:34]([N:44]2[CH2:49][CH2:48][N:47]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[CH2:46][CH2:45]2)[N:35]([CH2:40][C:41]#[C:42][CH3:43])[C:36]=1[C:37]([S:39][CH3:6])=[NH:38])([C:26]([CH3:28])([CH3:27])[CH3:29])([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 23070816HCID 23070816, compound

Product 1

HCID 59424141HCID 59424141, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1.23 g of trimethyloxonium tetrafluoroborate was added to a 100 ml dichloromethane solution of 4.351 g of t-butyl 4-[4-(t-butyldiphenylsilanyloxymethyl)-1-(2-butynyl)-5-thiocarbamoyl-1H-imidazol-2-yl]piperazine-1-carboxylate, and the mixture was stirred at room temperature for 15 hours. 300 ml of ethyl acetate was added to the solution, and the organic layer was washed successively with 100 ml of a saturated sodium bicarbonate solution and 100 ml a saturated ammonium chloride solution. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure to give 4.439 g of the title compound.

Workup

  1. washthe organic layer was washed successively with 100 ml of a saturated sodium bicarbonate solution and 100 ml a saturated ammonium chloride solution
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a7e4600881574c54bb86139c10d64b4e
Source dataset
uspto-grants-2010_08
Patent number
US07772226B2

Reaction notes

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