2-Iodoxybenzoic acid → HCID 23559956, compound

HRID 1057764Notes

Reaction equation

HRID 1057764 reaction equation
[C:1]([O:5][C:6]([C:8]1[NH:9][C:10]([I:17])=[C:11]([CH3:16])[C:12]=1[CH2:13][CH2:14][OH:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].I(C1C=CC=CC=1C(O)=O)(=O)=O>CS(C)=O.C(OCC)(=O)C>[C:1]([O:5][C:6]([C:8]1[NH:9][C:10]([I:17])=[C:11]([CH3:16])[C:12]=1[CH2:13][CH:14]=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 1087942-Iodoxybenzoic acidHCID 23559954HCID 23559954, compound

Product 1

HCID 23559956HCID 23559956, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(2-Hydroxy-ethyl)-5-iodo-4-methyl-1H-pyrrole-2-carboxylic acid tert-butyl ester (0.34 mmol, 114 mg) in DMSO (2 mL) was treated with o-iodoxybenzoic acid (IBX, 0.51 mmol, 148 mg), then held at room temperature for 3h. The mixture was diluted with ethyl acetate (50 mL), washed with brine (10 mL), then concentrated under reduced pressure to provide 84 mg (75%) of 5-iodo-4-methyl-3-(2-oxo-ethyl)-1H-pyrrole-2-carboxylic acid tert-butyl ester. 1H NMR (CDCl3) δ 9.63 (1H, s), 8.91 (1H, br s), 4.09 (2H, s), 2.62 (3H, s), 1.52 (9H, s).

Workup

  1. washwashed with brine (10 mL)
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5e8251202dc643799f00353f721a19bc
Source dataset
uspto-grants-2003_02
Patent number
US06514997B2

Reaction notes

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