Methanesulfonyl chloride → HCID 69673645, compound

HRID 1426348Notes

Reaction equation

HRID 1426348 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20](/[CH:22]=[N:23]/O)[CH:21]=1)[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1.CS(Cl)(=O)=O>N1C=CC=CC=1.C(OCC)(=O)C.[O-]S([O-])(=O)=O.[Cu+2]>[Br:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20]([C:22]#[N:23])[CH:21]=1)[O:5][CH:6]1[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:10][CH2:11]1

Participants

6

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 87944944HCID 87944944, compound

Product 1

HCID 69673645HCID 69673645, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolventHCID 24462Copper SulfateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl 4-{3-bromo-5-[(E)-(hydroxyimino)methyl]phenoxy}piperidine-1-carboxylate (157 mg, 0.393 mmol) in pyridine (1.2 mL) was added methanesulfonyl chloride (0.12 mL, 1.6 mmol). The reaction mixture was heated at 60° C. for 2 hours. The reaction solution was diluted with ethyl acetate and saturated CuSO4 solution. The organic layer was washed with CuSO4 twice, 1N HCl, brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on a silica gel column to give the desired product as white solid. LCMS (M+H)+: 381.1, 383.1.

Workup

  1. washThe organic layer was washed with CuSO4 twice
  2. dry with material1N HCl, brine, dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography on a silica gel column

Sources & evidence

ORD record
ord-05004a20c05640a1a78ab3130fd03182
Source dataset
uspto-grants-2015_01
Patent number
US08933085B2

Reaction notes

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