Water → (5R)-3-(6-{4-[3-(Cyclopentylthio)phenyl]butoxy}hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

HRID 2118322Notes

Reaction equation

HRID 2118322 reaction equation
[CH3:1][C:2]1([CH3:36])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@H:12]3[O:16][C:15](=[O:17])[N:14]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[C:31](I)[CH:30]=4)[CH2:13]3)=[CH:11][C:5]=2[CH2:4][O:3]1.C(N(CC)CC)C.[CH:44]1([SH:49])[CH2:48][CH2:47][CH2:46][CH2:45]1.O>CN1CCCC1=O.[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[Fe+2].[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[CH:44]1([S:49][C:31]2[CH:30]=[C:29]([CH2:28][CH2:27][CH2:26][CH2:25][O:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][N:14]3[CH2:13][C@@H:12]([C:10]4[CH:9]=[CH:8][C:6]5[O:7][C:2]([CH3:1])([CH3:36])[O:3][CH2:4][C:5]=5[CH:11]=4)[O:16][C:15]3=[O:17])[CH:34]=[CH:33][CH:32]=2)[CH2:48][CH2:47][CH2:46][CH2:45]1

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 15510CyclopentanethiolHCID 69120002(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-3-{6-[4-(3-iodophenyl)butoxy]hexyl}-1,3-oxazolidin-2-one

Product 1

HCID 69119396(5R)-3-(6-{4-[3-(Cyclopentylthio)phenyl]butoxy}hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 3

HCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 152416121,1`-Bis(diphenylphosphino)ferroceneCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
60 °C

Procedure

A stirred solution of (5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-3-{6-[4-(3-iodophenyl)butoxy]hexyl}-1,3-oxazolidin-2-one (1.8 g), 1,1 bis(diphenylphosphino) ferrocene (86 mg) and tris(dibenzylideneacetone) di palladium (180 mg) was stirred at room temperature in 1-methyl-2-pyrrolidinone (10 ml) and triethylamine (2 ml) for 10 min under nitrogen. Cyclopentyl mercaptan (0.63 ml) was added and the mixture was heated at 60° C. for 1 h. The mixture was cooled, poured into water and extracted into dichloromethane. The extracts were dried (Na2SO4) and evaporated. The residual oil was purified on a biotage cartridge (90 g) using ether-hexane (3:2) as eluent changing to ether. The appropriate fractions were evaporated to give the title compound (1.07 g).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted into dichloromethane
  3. dry with materialThe extracts were dried (Na2SO4)
  4. customevaporated
  5. customThe residual oil was purified on a biotage cartridge (90 g)
  6. customThe appropriate fractions were evaporated

Sources & evidence

ORD record
ord-51faa41fb1734125b203a2b3e1d5a980
Source dataset
uspto-grants-2008_10
Patent number
US07442839B2

Reaction notes

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