N-Iodosuccinimide → HCID 24773447, compound

HRID 1891187Notes

Reaction equation

HRID 1891187 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[C:15]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:14]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:13][C:12]=2[O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[O:8][N:7]=1)=[O:5])[CH3:2].[I:37]N1C(=O)CCC1=O>C(#N)C>[CH2:1]([NH:3][C:4]([C:6]1[C:10]([I:37])=[C:9]([C:11]2[CH:16]=[C:15]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:14]([O:21][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[CH:13][C:12]=2[O:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[O:8][N:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 247733585-(2,4-Bis-benzyloxy-5-isobutyl-phenyl)-isoxazole-3-carboxylic acid ethylamide

Product 1

HCID 24773447HCID 24773447, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-(2,4-Bis-benzyloxy-5-isobutyl-phenyl)-isoxazole-3-carboxylic acid ethylamide (1 eq) and N-iodosuccinimide (2.0 eq), were dissolved in acetonitrile, ceric ammonium nitrate (0.1 eq) added and the solution was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo and the resulting gum was partitioned between ethyl acetate and brine. The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography, eluting with 4:1 hexane:ethyl acetate, to give 5-(2,4-bis-benzyloxy-5-isobutyl-phenyl)-4-iodo-isoxazole-3-carboxylic acid ethylamide as an oil.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe resulting gum was partitioned between ethyl acetate and brine
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography
  7. washeluting with 4:1 hexane

Sources & evidence

ORD record
ord-ee6d289c1c8349dba9e2b65e28c959b0
Source dataset
uspto-grants-2013_08
Patent number
US08507480B2

Reaction notes

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