Methanesulfonyl chloride → HCID 68817382, compound

HRID 736722Notes

Reaction equation

HRID 736722 reaction equation
Cl.[CH3:2][C:3]1[CH:12]=[C:11]([CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([S:21]([NH:24][C@H:25]3[CH2:29][NH:28][CH2:27][C@H:26]3[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])(=[O:23])=[O:22])=[CH:17][CH:16]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>CN(C)C=O.CCN(C(C)C)C(C)C>[CH3:2][C:3]1[CH:12]=[C:11]([CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([S:21]([NH:24][C@H:25]3[CH2:29][N:28]([S:38]([CH3:37])(=[O:40])=[O:39])[CH2:27][C@H:26]3[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])(=[O:23])=[O:22])=[CH:17][CH:16]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 68818823HCID 68818823, compound

Product 1

HCID 68817382HCID 68817382, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 81531DiisopropylethylamineSolvent

Procedure

To the stirred solution of 373 mg of tert-butyl cis-4-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]pyrrolidine-3-carboxylate hydrochloride in 8 mL of N,N-dimethylformamide and 0.5 mL of Hunig's base was slowly added 104 mg of methanesulfonyl chloride. The solution was stirred at room temperature overnight. After removal of the N,N-dimethylformamide in vacuo, the residue was dissolved in 80 mL of ethyl acetate. The ethyl acetate solution was washed with water and saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate/hexane to provide 233 mg of tert-butyl cis-4-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]-1-(methylsulfonyl)pyrrolidine-3-carboxylate in 58% yield. MS: 576.1 (M+H)+

Workup

  1. customAfter removal of the N,N-dimethylformamide in vacuo
  2. dissolutionthe residue was dissolved in 80 mL of ethyl acetate
  3. washThe ethyl acetate solution was washed with water and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica gel eluting with ethyl acetate/hexane

Sources & evidence

ORD record
ord-1788a2f318f14cc29e647e8698f51c62
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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