Water → HCID 23518868, compound

HRID 859177Notes

Reaction equation

HRID 859177 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:24])[C:14]2[CH:19]=[CH:18][C:17]([N:20]=[N+:21]=[N-:22])=[CH:16][C:15]=2[OH:23])=[CH:8][N:7]=1.[I-:26].[Na+].CC1C=CC(S(NCl)(=O)=O)=CC=1.O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:25])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:24])[C:14]2[CH:19]=[C:18]([I:26])[C:17]([N:20]=[N+:21]=[N-:22])=[CH:16][C:15]=2[OH:23])=[CH:8][N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 31388TosylchloramideHCID 15980921HCID 15980921, compound

Product 1

HCID 23518868HCID 23518868, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of (5-(4-azido-2-hydroxybenzoylamino)pyridin-2-yloxy)acetic acid methyl ester (22 mg, 0.064 mmol) in DMF (1 mL) was added sodium iodide (11 mg, 0.07 mmol) and chloramine T (51 mg, 0.22 mol). The reaction mixture turned homogeneous and after 10 minutes, the mixture was poured into water and was extracted with ethyl acetate (3×25 mL). The combined extracts were washed with water and brine and dried over magnesium sulfate. Filtration and concentration in vacuo gave a residue that was purified via radial chromatography (1 mm plate, 10% ethyl acetate/hexanes as eluant). This gave 7.8 mg (26%) of (5-(4-azido-2-hydroxy-5-iodo-benzoylamino)-pyridin-2-yloxy)-acetic acid methyl ester as an off-white solid: 1H NMR (300 MHz, acetone-d6) δ 9.92 (bs, 1H) 8.40 (m, 1H), 8.33 (s, 1H), 8.05 (m, 1H), 6.92 (m, 1H), 6.87 (s, 1H), 4.90 (s, 2H), 3.69 (s, 3H); MS (EI) m/z 467.97 (M−H)−.

Workup

  1. extractionwas extracted with ethyl acetate (3×25 mL)
  2. washThe combined extracts were washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationFiltration and concentration in vacuo
  5. customgave a residue that
  6. customwas purified via radial chromatography (1 mm plate, 10% ethyl acetate/hexanes as eluant)

Sources & evidence

ORD record
ord-6d90c7eb227742ec9b7333522315cc60
Source dataset
uspto-grants-2006_12
Patent number
US07151112B1

Reaction notes

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