Methanesulfonamide → HCID 66634221, compound

HRID 537385Notes

Reaction equation

HRID 537385 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]/[CH3:10].CC[C@H]1[C@H]2C[C@H]([C@H](OC3C4C(=CC=CC=4)C(O[C@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C([O:32]C)C=C4)N(CC2)C1.CS(N)(=O)=O.CC(O)(C)C.[OH2:79]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@@H:8]([OH:32])[C@H:9]([OH:79])[CH3:10]

Participants

5

Reactant 4

HCID 72879MethanesulfonamideHCID 144196771-Chloro-2-[(1E)-prop-1-en-1-yl]benzeneHCID 510036741-((1R)-((2R,4R,5S)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)-4-((1R)-((2R,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)phthalazineHCID 714019492-Methylpropan-2-ol--water (1/1)

Product 1

HCID 66634221HCID 66634221, compoundYield 90%

Procedure

1-(2-chlorophenyl)-trans-1-propene (2.5 g, Preparation Example 1) was dissolved in 50 mL of the mixture of t-BuOH/H2O (1:1 (V/V)). At 0° C., AD-mix-α (Aldrich, U.S.A.) (23.5 g) and methane sulfone amide (CH3SO2NH2, 1.27 g, 0.013 mol) were added thereto and stirred for overnight. When the reaction was completed, the obtained product was washed with an aqueous solution of sodium sulfite (Na2SO3) and ethylacetate (EA). Then, the organic layer was dehydrated with anhydrous magnesium sulfate (MgSO4), filtrated, and concentrated under reduced pressure. The concentrated residue was purified by a silica gel column chromatography to produce the title compound (2.96 g, yield 90%).

Workup

  1. washthe obtained product was washed with an aqueous solution of sodium sulfite (Na2SO3) and ethylacetate (EA)
  2. filtrationfiltrated
  3. concentrationconcentrated under reduced pressure
  4. customThe concentrated residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-6f6223f9096b46d79c6e20853e4b6878
Source dataset
uspto-grants-2014_10
Patent number
US08859817B2

Reaction notes

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