Benzenesulfonyl chloride → N-[3-([2-({6-[(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)ethoxy]methyl)phenyl]-3-[(phenylsulfonyl)amino]-benzamide

HRID 2369697Notes

Reaction equation

HRID 2369697 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:43]=[CH:44][CH:45]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][N:25]2[CH2:29][C@@H:28]([C:30]3[CH:41]=[CH:40][C:33]4[O:34][C:35]([CH3:39])([CH3:38])[O:36][CH2:37][C:32]=4[CH:31]=3)[O:27][C:26]2=[O:42])[CH:9]=1)=[O:6].[C:46]1([S:52](Cl)(=[O:54])=[O:53])[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[CH3:38][C:35]1([CH3:39])[O:34][C:33]2[CH:40]=[CH:41][C:30]([C@H:28]3[O:27][C:26](=[O:42])[N:25]([CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][O:18][CH2:17][CH2:16][O:15][CH2:14][C:10]4[CH:9]=[C:8]([NH:7][C:5](=[O:6])[C:4]5[CH:43]=[CH:44][CH:45]=[C:2]([NH:1][S:52]([C:46]6[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=6)(=[O:54])=[O:53])[CH:3]=5)[CH:13]=[CH:12][CH:11]=4)[CH2:29]3)=[CH:31][C:32]=2[CH2:37][O:36]1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 668448583-Amino-N-[3-({2-({6-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)ethoxy}methyl)phenyl]benzamide

Product 1

HCID 66845591N-[3-([2-({6-[(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)ethoxy]methyl)phenyl]-3-[(phenylsulfonyl)amino]-benzamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Amino-N-[3-({2-({6-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)ethoxy}methyl)phenyl]benzamide (200 mg) in pyridine (5 ml) under nitrogen was treated with benzenesulfonyl chloride (0.045 ml) and the mixture was stirred at 20° for 2 h. Sat. sodium bicarbonate solution (30 ml) was added and the mixture was extracted with dichloromethane (2×20 ml). The combined extracts were dried (Na2SO4) and the solvent evaporated in vacuo. The residue was purified by flash chromatography on silica gel. Elution with EtOAc-dichloromethane (1:1) gave the title compound (155 mg). LCMS RT=3.72 min, ES+ve 758 (MH)+.

Workup

  1. extractionthe mixture was extracted with dichloromethane (2×20 ml)
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. customthe solvent evaporated in vacuo
  4. customThe residue was purified by flash chromatography on silica gel
  5. washElution with EtOAc-dichloromethane (1:1)

Sources & evidence

ORD record
ord-eee7cf8011854ff1b7a985ab31445a03
Source dataset
uspto-grants-2014_04
Patent number
USRE044874E1

Reaction notes

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