Methanesulfonyl chloride → HCID 59312563, compound

HRID 885847Notes

Reaction equation

HRID 885847 reaction equation
[CH3:1][S:2]([Cl:5])(=[O:4])=[O:3].[OH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([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:10][CH:9]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl.CN(C=O)C.O>[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:11]2[CH:10]=[CH:9][C:8]([CH2:7][O:6][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:13][CH:12]=2)=[O:35])=[CH:18][CH:19]=1)=[O:26].[Cl:5][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([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:10][CH:9]=1

Participants

8

Reactant 3

HCID 31297Methanesulfonyl chloride2×HCID 516892Sodium BicarbonateHCID 86641367HCID 86641367, compound

Product 2

HCID 59312563HCID 59312563, compoundHCID 86641368HCID 86641368, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (388 mg, 3.39 mmol) was added to a stirred solution of (E)-3-{4-[(E)-3-(4-hydroxymethyl-phenyl)-3-oxo-propenyl]-phenyl}-N-(tetrahydro-pyran-2-yloxy)-acrylamide (1.15 g, 2.82 mmol) and TEA (1.18 ml, 8.46 mmol) in DCM (20 ml) and DMF (20 ml). The mixture was stirred at room temperature for 1 h and then additional methanesulfonyl chloride (258 mg, 2.25 mmol) and TEA (0.393 ml, 2.82 mmol) were added. After stirring for additional 1 h the solution was diluted with water and brought to basic conditions with 5% NaHCO3. The resulting slurry was extracted with AcOEt 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 277 mg of the title compound and 423 mg of (E)-3-{4-[(E)-3-(4-chloromethyl-phenyl)-3-oxo-propenyl]-phenyl}-N-(tetrahydro-pyran-2-yloxy)-acrylamide.

Workup

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

Sources & evidence

ORD record
ord-2753694a5f3b4aaba106f9f48094e304
Source dataset
uspto-grants-2012_08
Patent number
US08242175B2

Reaction notes

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