Hydrochloric Acid → HCID 59599491, compound

HRID 2267073Notes

Reaction equation

HRID 2267073 reaction equation
S([O-])(O[O-])(=O)=[O:2].[K+].[K+].[C:9]([C:12]1[CH:35]=[CH:34][C:15]([O:16][CH2:17][C:18]2[CH:19]=[C:20]([S:24][C:25]3[CH:26]=[N:27][CH:28]=[C:29]([CH:33]=3)[C:30]([OH:32])=[O:31])[CH:21]=[CH:22][CH:23]=2)=[C:14]([CH3:36])[C:13]=1[OH:37])(=[O:11])[CH3:10].Cl>O.CO>[C:9]([C:12]1[CH:35]=[CH:34][C:15]([O:16][CH2:17][C:18]2[CH:19]=[C:20]([S:24]([C:25]3[CH:26]=[N:27][CH:28]=[C:29]([CH:33]=3)[C:30]([OH:32])=[O:31])=[O:2])[CH:21]=[CH:22][CH:23]=2)=[C:14]([CH3:36])[C:13]=1[OH:37])(=[O:11])[CH3:10]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10313463Potassium peroxymonosulphateHCID 59599561HCID 59599561, compound

Product 1

HCID 59599491HCID 59599491, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

Add a 0.5 M solution of potassium peroxymonosulfate (0.61 g, 1.00 mmol) in water (2.0 mL) to a solution of 5-(3-((4-acetyl-3-hydroxy-2-methylphenoxy)methyl)phenylthio)nicotinic acid (205 mg, 0.50 mmol) in methanol (7.5 mL) at 0° C. Allow the solution to warm to room temperature and stir for 1.5 d. Add water and 2.2 mL of 2.0 M HCl to the mixture. Extract the mixture with EtOAc. Dry, filter and concentrate. Recrystallize the residue from a mixture of CH2Cl2 and hexanes to give a light yellow solid. Purify the yellow solid by flash chromatograhpy on silica gel eluting with a mixture of acetone, hexanes, and acetic acid (50:50:1 to 90:10) to afford the title compound (31 mg, 15%): 1H NMR (d6-DMSO) δ 2.01 (s, 3H), 2.58 (s, 3H), 5.33 (s, 2H), 6.67 (d, J=9.0 Hz, 1H), 7.61-7.63 (m, 2H), 7.77 (d, J=9.0 Hz, 1H), 7.81-7.83 (m, 1H), 7.88 (s, 1H), 8.49 (t, J=2.0 Hz, 1H), 9.08 (d, J=2.0 Hz, 1H), 9.12 (d, J=2.0 Hz, 1H), 12.84 (s, 1H); MS (APCI-neg mode) m/z (rel intensity): 424 (M−H, 100%).

Workup

  1. extractionExtract the mixture with EtOAc
  2. customDry
  3. filtrationfilter
  4. concentrationconcentrate
  5. customRecrystallize the residue
  6. additionfrom a mixture of CH2Cl2 and hexanes
  7. customto give a light yellow solid
  8. customPurify the yellow solid by flash chromatograhpy on silica gel eluting
  9. additionwith a mixture of acetone, hexanes, and acetic acid (50:50:1 to 90:10)

Sources & evidence

ORD record
ord-f8c4e6f87be84db3b0dbae4b51c078ff
Source dataset
uspto-grants-2010_12
Patent number
US07858646B2

Reaction notes

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