N-Iodosuccinimide → 5-(2,4-Bis-benzyloxy-5-tert-butyl-phenyl)-4-iodo-isoxazole-3-carboxylic acid ethylamide

HRID 2097283Notes

Reaction equation

HRID 2097283 reaction equation
[I:1]N1C(=O)CCC1=O.[CH2:9]([NH:11][C:12]([C:14]1[CH:18]=[C:17]([C:19]2[CH:24]=[C:23]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:22]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:21][C:20]=2[O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[O:16][N:15]=1)=[O:13])[CH3:10]>C(#N)C.[N+]([O-])([O-])=O.[Ce].[NH4+]>[CH2:9]([NH:11][C:12]([C:14]1[C:18]([I:1])=[C:17]([C:19]2[CH:24]=[C:23]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:22]([O:29][CH2:30][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)=[CH:21][C:20]=2[O:37][CH2:38][C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[O:16][N:15]=1)=[O:13])[CH3:10]

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 247733555-(2,4-Bis-benzyloxy-5-tert-butyl-phenyl)-isoxazole-3-carboxylic acid ethylamide

Product 1

HCID 247734485-(2,4-Bis-benzyloxy-5-tert-butyl-phenyl)-4-iodo-isoxazole-3-carboxylic acid ethylamideYield 62.2%

Reagents, catalysts & solvents 2

HCID 57418452Ammonium cerium-nitrateCatalystHCID 6342AcetonitrileSolvent

Procedure

N-iodosuccinimide (9.0 g, 40 mmol) was added to a suspension of 5-(2,4-Bis-benzyloxy-5-tert-butyl-phenyl)-isoxazole-3-carboxylic acid ethylamide (9.9 g, 20.4 mmol) in acetonitrile (60 ml). Ammonium cerium nitrate (0.25 g, 0.46 mmol) was added and the suspension stirred for ˜18 hrs. The resulting suspension was concentrated and the residue taken up in dichloromethane (125 ml). The resulting solution was washed aqueous sodium metabisulphite solution (2×100 ml, 5%), water (100 ml) and saturated aqueous sodium chloride solution (100 ml). The solution was dried over anhydrous sodium sulphate and concentrated to a pale red gum. Trituration with ethanol (25 ml) gave an off-white solid, solids were removed by filtration and washed with ethanol. Dried in vacuo (40° C.), to give 5-(2,4-Bis-benzyloxy-5-tert-butyl-phenyl)-4-iodo-isoxazole-3-carboxylic acid ethylamide as an off-white powder (7.75 g, 62%).

Workup

  1. concentrationThe resulting suspension was concentrated
  2. washThe resulting solution was washed aqueous sodium metabisulphite solution (2×100 ml, 5%), water (100 ml) and saturated aqueous sodium chloride solution (100 ml)
  3. dry with materialThe solution was dried over anhydrous sodium sulphate
  4. concentrationconcentrated to a pale red gum
  5. customTrituration with ethanol (25 ml) gave an off-white solid, solids
  6. customwere removed by filtration
  7. washwashed with ethanol
  8. customDried in vacuo (40° C.)

Sources & evidence

ORD record
ord-cbcf91fe31694801810bc6850cc0b4ab
Source dataset
uspto-grants-2013_05
Patent number
US08450310B2

Reaction notes

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