Methanesulfonyl chloride → HCID 59312564, compound

HRID 885852Notes

Reaction equation

HRID 885852 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][C:8]1[CH:9]=[C:10]([C:14](=[O:35])/[CH:15]=[CH:16]/[C:17]2[CH:22]=[CH:21][C:20](/[CH:23]=[CH:24]/[C:25]([NH:27][O:28][CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][O:30]3)=[O:26])=[CH:19][CH:18]=2)[CH:11]=[CH:12][CH:13]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl.CN(C=O)C>[O:30]1[CH2:31][CH2:32][CH2:33][CH2:34][CH:29]1[O:28][NH:27][C:25](/[CH:24]=[CH:23]/[C:20]1[CH:21]=[CH:22][C:17](/[CH:16]=[CH:15]/[C:14]([C:10]2[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=2)[CH2:7][O:6][S:2]([CH3:1])(=[O:4])=[O:3])=[O:35])=[CH:18][CH:19]=1)=[O:26]

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 86641369HCID 86641369, compound

Product 1

HCID 59312564HCID 59312564, compoundYield 46.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (0.41 ml, 5.3 mmol) was added to a stirred solution of (E)-3-{4-[(E)-3-(3-hydroxymethyl-phenyl)-3-oxo-propenyl]-phenyl}-N-(tetrahydro-pyran-2-yloxy)-acrylamide (1.08 g, 2.68 mmol) and TEA (1.47 ml, 10.6 mmol) in DCM (18 ml) and DMF (12 ml). The mixture was stirred at room temperature for 30 min and then brought to basic conditions with 5% NaHCO3. The resulting slurry was extracted with Et2O and the organic phase was washed with water, dried over Na2SO4 and evaporated in vacuo. The crude reaction mixture was purified by column chromatography (eluent: petroleum ether/AcOEt 1:1) to give 600 mg of a mixture of the title compound and (E)-3-{4-[(E)-3-(3-chloromethyl-phenyl)-3-oxo-propenyl]-phenyl}-N-(tetrahydro-pyran-2-yloxy)-acrylamide as the main product.

Workup

  1. extractionThe resulting slurry was extracted with Et2O
  2. washthe organic phase was washed with water
  3. dry with materialdried over Na2SO4
  4. customevaporated in vacuo
  5. customThe crude reaction mixture
  6. customwas purified by column chromatography (eluent: petroleum ether/AcOEt 1:1)

Sources & evidence

ORD record
ord-325ca64576114d0db10606d295dfa6ac
Source dataset
uspto-grants-2012_08
Patent number
US08242175B2

Reaction notes

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