Methanesulfonyl chloride → HCID 86592860, compound

HRID 351270Notes

Reaction equation

HRID 351270 reaction equation
[C:1]([O:5][C:6](=[O:32])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[N:18]=[C:17]([C:28](O)([CH3:30])[CH3:29])[CH:16]=2)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].CS(Cl)(=O)=O>CCN(CC)CC>[C:28]([C:17]1[CH:16]=[C:15]([C:12]2[CH:11]=[CH:10][C:9]([CH2:8][NH:7][C:6](=[O:32])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:14][CH:13]=2)[N:19]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[N:18]=1)([CH3:30])=[CH2:29]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 91605231HCID 91605231, compound

Product 1

HCID 86592860HCID 86592860, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of tert-butyl{4-[3-(1-hydroxy-1-methyl-ethyl)-1-(4-methoxyphenyl)-1H-pyrazol-5-yl]benzyl}-carbamate (1.1 g) and Et3N (1.02 g) was added methane sulfonyl chloride (576 mg). The mixture was stirred at ambient temperature overnight. The mixture was concentrated in vacuo. The residue was partitioned between AcOEt and 1M HCl. The organic layer was separated, washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography eluted with AcOEt/n-hexane=25%. The pure fraction was collected and concentrated in vacuo to give tert-butyl {4-[3-isopropenyl-1-(4-methoxyphenyl)-1-H-pyrazol-5-yl]benzyl}carbamate (857 mg) as a solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe residue was partitioned between AcOEt and 1M HCl
  3. customThe organic layer was separated
  4. washwashed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography
  8. washeluted with AcOEt/n-hexane=25%
  9. customThe pure fraction was collected
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-829e12dd1f7842a691ae85fb024600c3
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

Loading…