(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one → (5R)-3-(6-(2-((2,6-dichlorophenyl)methoxy)ethoxy)hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

HRID 1014852Notes

Reaction equation

HRID 1014852 reaction equation
CC(C)([O-])C.[K+].[CH3:7][C:8]1([CH3:24])[O:13][C:12]2[CH:14]=[CH:15][C:16]([C@H:18]3[O:22][C:21](=[O:23])[NH:20][CH2:19]3)=[CH:17][C:11]=2[CH2:10][O:9]1.Br[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][O:35][CH2:36][C:37]1[C:42]([Cl:43])=[CH:41][CH:40]=[CH:39][C:38]=1[Cl:44]>CN(C=O)C>[Cl:43][C:42]1[CH:41]=[CH:40][CH:39]=[C:38]([Cl:44])[C:37]=1[CH2:36][O:35][CH2:34][CH2:33][O:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][N:20]1[CH2:19][C@@H:18]([C:16]2[CH:15]=[CH:14][C:12]3[O:13][C:8]([CH3:24])([CH3:7])[O:9][CH2:10][C:11]=3[CH:17]=2)[O:22][C:21]1=[O:23]

Participants

5

Reactant 3

HCID 10933894(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-oneHCID 23665647Potassium tert-butoxideHCID 668449032-((2-((6-Bromohexyl)oxy)ethoxy)methyl)-1,3-dichlorobenzene

Product 1

HCID 46833391(5R)-3-(6-(2-((2,6-dichlorophenyl)methoxy)ethoxy)hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-oneYield 100.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Potassium tert-butoxide (4.38 g, 39 mmol) was added to a solution of (5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (9.3 g, 39 mmol) in anhydrous DMF (100 mL) under N2 and the reaction stirred for 1 h at ambient temperature. A solution of 2-[2-(6-bromo-hexyloxy)-ethoxymethyl]-1,3-dichloro-benzene (15 g, 39 mmol) in anhydrous DMF (25 mL) was added and the reaction allowed to stir at ambient temperature for 20 h. The reaction mixture was poured into ice/water (350 mL) and extracted with ethyl acetate (300 mL). The organic layer was separated then washed successively with water/saturated brine (250 mL/25 mL), water/brine (25 mL/10 mL) and finally brine (150 mL), before drying over sodium sulfate. The solution was concentrated to dryness under vacuum to afford the title compound as an oil (21.6 g)—LC RT=6.8 min.

Workup

  1. stirringto stir at ambient temperature for 20 h
  2. extractionextracted with ethyl acetate (300 mL)
  3. customThe organic layer was separated
  4. washthen washed successively with water/saturated brine (250 mL/25 mL), water/brine (25 mL/10 mL) and finally brine (150 mL)
  5. dry with materialbefore drying over sodium sulfate
  6. concentrationThe solution was concentrated to dryness under vacuum

Sources & evidence

ORD record
ord-f9d2b383b8b94d60b9c7f93f81004b0b
Source dataset
uspto-grants-2011_07
Patent number
US07982067B2

Reaction notes

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