Ethyl isocyanate → 3-[4-({6-[(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)butyl]-N-[(ethylamino)carbonyl]benzenesulfonamide

HRID 720834Notes

Reaction equation

HRID 720834 reaction equation
[CH2:1]([N:3]=[C:4]=[O:5])[CH3:2].[CH3:6][C:7]1([CH3:44])[O:12][C:11]2[CH:13]=[CH:14][C:15]([C@H:17]3[O:21][C:20](=[O:22])[N:19]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]4[CH:35]=[C:36]([S:40]([NH2:43])(=[O:42])=[O:41])[CH:37]=[CH:38][CH:39]=4)[CH2:18]3)=[CH:16][C:10]=2[CH2:9][O:8]1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:6][C:7]1([CH3:44])[O:12][C:11]2[CH:13]=[CH:14][C:15]([C@H:17]3[O:21][C:20](=[O:22])[N:19]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]4[CH:35]=[C:36]([S:40]([NH:43][C:4]([NH:3][CH2:1][CH3:2])=[O:5])(=[O:42])=[O:41])[CH:37]=[CH:38][CH:39]=4)[CH2:18]3)=[CH:16][C:10]=2[CH2:9][O:8]1

Participants

5

Reactant 3

HCID 8022Ethyl isocyanate2×HCID 11430Potassium CarbonateHCID 426252493-[4-({6-[(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)butyl]benzenesulfonamide

Product 1

HCID 691973193-[4-({6-[(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)butyl]-N-[(ethylamino)carbonyl]benzenesulfonamideYield 54.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ethyl isocyanate (0.015 g) was added to a stirred mixture of 3-[4-({6-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)butyl]benzenesulfonamide (0.11 g) and K2CO3 (0.055 g) in acetone (2 ml). The mixture was heated at reflux for 2 h then ethyl isocyanate (0.005 g) was added. After 0.5 h the reaction mixture was cooled and quenched with water (1 ml). The mixture was partitioned between EtOAc (20 ml) and H2O (20 ml). The aqueous phase was extracted with EtOAc (20 ml). The combined EtOAc phases were washed with brine (10 ml) then dried (Na2SO4) and concentrated. The residue was purified by SPE (silica 5 g) with CH2Cl2 (2×15 ml), Et2O (2×15 ml) and EtOAc (2×15 ml), evaporation of the EtOAc fractions afforded the title compound (0.067 g). ES+ve 632 (MH)+

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h
  3. temperatureAfter 0.5 h the reaction mixture was cooled
  4. customquenched with water (1 ml)
  5. customThe mixture was partitioned between EtOAc (20 ml) and H2O (20 ml)
  6. extractionThe aqueous phase was extracted with EtOAc (20 ml)
  7. washThe combined EtOAc phases were washed with brine (10 ml)
  8. dry with materialthen dried (Na2SO4)
  9. concentrationconcentrated
  10. customThe residue was purified by SPE (silica 5 g) with CH2Cl2 (2×15 ml), Et2O (2×15 ml) and EtOAc (2×15 ml), evaporation of the EtOAc fractions

Sources & evidence

ORD record
ord-ef2d7e3ded2e4ad4bc1a260708e2d69c
Source dataset
uspto-grants-2006_11
Patent number
US07135600B2

Reaction notes

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