Sodium hydride → (5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-3-{6-[4-(3-iodophenyl)butoxy]hexyl}-1,3-oxazolidin-2-one

HRID 2118321Notes

Reaction equation

HRID 2118321 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:20])[O:9][C:8]2[CH:10]=[CH:11][C:12]([C@H:14]3[O:18][C:17](=[O:19])[NH:16][CH2:15]3)=[CH:13][C:7]=2[CH2:6][O:5]1.[I:21][C:22]1[CH:23]=[C:24]([CH2:28][CH2:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]Br)[CH:25]=[CH:26][CH:27]=1.[Cl-].[NH4+]>CN(C=O)C>[CH3:3][C:4]1([CH3:20])[O:9][C:8]2[CH:10]=[CH:11][C:12]([C@H:14]3[O:18][C:17](=[O:19])[N:16]([CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][O:32][CH2:31][CH2:30][CH2:29][CH2:28][C:24]4[CH:25]=[CH:26][CH:27]=[C:22]([I:21])[CH:23]=4)[CH2:15]3)=[CH:13][C:7]=2[CH2:6][O:5]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 10933894(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-oneHCID 691198836-Bromohexyl 4-(3-iodophenyl)butyl ether

Product 1

HCID 69120002(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-3-{6-[4-(3-iodophenyl)butoxy]hexyl}-1,3-oxazolidin-2-oneYield 73.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

Sodium hydride (60% dispersion in oil 1.26 g) was added to a stirred, cooled (ice-bath) solution of (5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxazolidinone (5.47 g) in dry DMF (50 ml) under nitrogen and the mixture was stirred for 15 min at 50° C. A solution of 6-bromohexyl 4-(3-iodophenyl)butyl ether (10.7 g) in DMF (30 ml) was then added dropwise over 10 min. The mixture was stirred for 2 h at ambient temperature, then poured into aqueous solution of ammonium chloride and extracted into ethyl acetate. The combined extracts were washed with water, dried (Na2SO4) and evaporated. The residue was purified on biotage (90 g cartridge) eluting with ether-hexane (3:2) to give the title compound (9.8 g). LCMS RT=4.20 min.

Workup

  1. stirringThe mixture was stirred for 2 h at ambient temperature
  2. extractionextracted into ethyl acetate
  3. washThe combined extracts were washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was purified on biotage (90 g cartridge)
  7. washeluting with ether-hexane (3:2)

Sources & evidence

ORD record
ord-de1f4bb28dc541d7baf2ede4bb30bacc
Source dataset
uspto-grants-2008_10
Patent number
US07442839B2

Reaction notes

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