Methanesulfonyl chloride → N-(3-{[2-(4-{2-[(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]ethyl}phenoxy)ethoxy]methyl}phenyl)methanesulfonamide

HRID 916808Notes

Reaction equation

HRID 916808 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:36]=[CH:37][CH:38]=1)[CH2:5][O:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][N:18]2[CH2:22][C@@H:21]([C:23]3[CH:34]=[CH:33][C:26]4[O:27][C:28]([CH3:32])([CH3:31])[O:29][CH2:30][C:25]=4[CH:24]=3)[O:20][C:19]2=[O:35])=[CH:12][CH:11]=1.[CH3:39][S:40](Cl)(=[O:42])=[O:41]>N1C=CC=CC=1>[CH3:31][C:28]1([CH3:32])[O:27][C:26]2[CH:33]=[CH:34][C:23]([C@H:21]3[O:20][C:19](=[O:35])[N:18]([CH2:17][CH2:16][C:13]4[CH:12]=[CH:11][C:10]([O:9][CH2:8][CH2:7][O:6][CH2:5][C:4]5[CH:3]=[C:2]([NH:1][S:40]([CH3:39])(=[O:42])=[O:41])[CH:38]=[CH:37][CH:36]=5)=[CH:15][CH:14]=4)[CH2:22]3)=[CH:24][C:25]=2[CH2:30][O:29]1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 11295328(5R)-3-[2-(4-{2-[(3-Aminobenzyl)oxy]ethoxy}phenyl)ethyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

Product 1

HCID 69386578N-(3-{[2-(4-{2-[(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]ethyl}phenoxy)ethoxy]methyl}phenyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (5R)-3-[2-(4-[2-[(3-aminobenzyl)oxy]ethoxy}phenyl)ethyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (Example 1 xii)) (117 mg) in pyridine (10 mL) was stirred with methanesulfonyl chloride (39 mg) at 20° C. for 90 min. The reaction mixture was partitioned between aqueous NaHCO3 and DCM. The organic solution was dried (Na2SO4), and the solvent was removed in vacuo to yield the title compound (138 mg). LCMS RT=3.30 min

Workup

  1. customThe reaction mixture was partitioned between aqueous NaHCO3 and DCM
  2. dry with materialThe organic solution was dried (Na2SO4)
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-e29e8e11b8cc4cfc87dc394a1220dbed
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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