2-Iodoxybenzoic acid → HCID 117928482, compound

HRID 1055501Notes

Reaction equation

HRID 1055501 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@@H:14]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@:13]2([C:33]3[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([CH2:40][C:41]4[CH:46]=[CH:45][C:44]([O:47][CH2:48][CH3:49])=[CH:43][CH:42]=4)[CH:34]=3)[O:32][C@@:10]1([CH2:50][OH:51])[CH2:11][O:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I(C1C=CC=CC=1C(O)=O)(=O)=O>ClCCl>[CH2:1]([O:8][C@H:9]1[C@H:15]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C@@H:14]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@:13]2([C:33]3[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([CH2:40][C:41]4[CH:42]=[CH:43][C:44]([O:47][CH2:48][CH3:49])=[CH:45][CH:46]=4)[CH:34]=3)[O:32][C@@:10]1([CH:50]=[O:51])[CH2:11][O:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1087942-Iodoxybenzoic acidHCID 67153941HCID 67153941, compound

Product 1

HCID 117928482HCID 117928482, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of [(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]methanol 1j (8.53 g, 12.08 mmol) in dichloromethane (350 mL) was added 2-iodoxybenzoicacid (6.77 g, 24.2 mmol) at room temperature. The mixture was refluxed at 45° C. for 36 hours and quenched with 150 mL of water. The mixture was partitioned between dichloromethane and water. The organic layer was washed with saturated aqueous sodium chloride (150 mL×2), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluted with PE/EtOAc(v/v)=10/1 to give the title compound 1k as pale yellow oil (4.94 g, 60.0%).

Workup

  1. customquenched with 150 mL of water
  2. customThe mixture was partitioned between dichloromethane and water
  3. washThe organic layer was washed with saturated aqueous sodium chloride (150 mL×2)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography
  7. washeluted with PE/EtOAc(v/v)=10/1

Sources & evidence

ORD record
ord-4aca6ec68f3e4933a5175ceacdc1d745
Source dataset
uspto-grants-2016_07
Patent number
US09394329B2

Reaction notes

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