1-(Cyclopentylsulfonyl)-3-iodobenzene → (5R)-3-[6-({5-[3-(Cyclopentylsulfonyl)phenyl]-4-pentyn-1-yl}oxy)hexyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

HRID 2118340Notes

Reaction equation

HRID 2118340 reaction equation
[CH3:1][C:2]1([CH3:30])[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][C:28]#[CH:29])[CH2:13]3)=[CH:11][C:5]=2[CH2:4][O:3]1.[CH:31]1([S:36]([C:39]2[CH:44]=[CH:43][CH:42]=[C:41](I)[CH:40]=2)(=[O:38])=[O:37])[CH2:35][CH2:34][CH2:33][CH2:32]1>CC#N.C(N(CC)CC)C>[CH:31]1([S:36]([C:39]2[CH:40]=[C:41]([C:29]#[C: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]([CH3:30])([CH3:1])[O:3][CH2:4][C:5]=5[CH:11]=4)[O:16][C:15]3=[O:17])[CH:42]=[CH:43][CH:44]=2)(=[O:37])=[O:38])[CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

5

Reactant 2

HCID 691197141-(Cyclopentylsulfonyl)-3-iodobenzeneHCID 86607678(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-3-[6-(4-pentyn-1-yloxy)hexyl]-1,3-oxazolidin-2-one

Product 1

HCID 69119922(5R)-3-[6-({5-[3-(Cyclopentylsulfonyl)phenyl]-4-pentyn-1-yl}oxy)hexyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-oneYield 78.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

A solution of (5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-3-[6-(4-pentyn-1-yloxy)hexyl]-1,3-oxazolidin-2-one (207 mg) and 1-(cyclopentylsulfonyl)-3-iodobenzene (Example 8iii.) (202 mg) in MeCN (8 ml) and triethylamine (4 ml) was deoxygenated by bubbling a nitrogen stream through for 10 min. Copper (I) iodide (10 mg) and dichlorobis(triphenylphosphine)palladium (II) (18 mg) were added and the mixture stirred at 20° for 4 h. The solvent was evaporated in vacuo and the residues purified by using a SPE silica bond elut cartridge (10 g, silica). Elution with DCM (1vol), EtOAc-cyclohexane (1:4) (3vols), (1:3) (1vol) then (1:1) (3vols) gave the title compound (243 mg). LCMS RT=3.79 min.

Workup

  1. customby bubbling a nitrogen stream through for 10 min
  2. additionCopper (I) iodide (10 mg) and dichlorobis(triphenylphosphine)palladium (II) (18 mg) were added
  3. customThe solvent was evaporated in vacuo
  4. customthe residues purified
  5. washElution with DCM (1vol), EtOAc-cyclohexane (1:4) (3vols), (1:3) (1vol)

Sources & evidence

ORD record
ord-6dd2f8f0243e4113a17220fff5ea6095
Source dataset
uspto-grants-2008_10
Patent number
US07442839B2

Reaction notes

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