Methanol → 3-hydroxy-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}-N-(5-methylpyrazin-2-yl)benzamide

HRID 1990043Notes

Reaction equation

HRID 1990043 reaction equation
C[Si](I)(C)C.[OH:6][C:7]1[CH:8]=[C:9]([CH:20]=[C:21]([O:23][C@@H:24]([CH3:28])[CH2:25][O:26]C)[CH:22]=1)[C:10]([NH:12][C:13]1[CH:18]=[N:17][C:16]([CH3:19])=[CH:15][N:14]=1)=[O:11].CO.O.O.O.O.O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C>[OH:6][C:7]1[CH:8]=[C:9]([CH:20]=[C:21]([O:23][C@@H:24]([CH3:28])[CH2:25][OH:26])[CH:22]=1)[C:10]([NH:12][C:13]1[CH:18]=[N:17][C:16]([CH3:19])=[CH:15][N:14]=1)=[O:11]

Participants

6

Reactant 4

HCID 887MethanolHCID 61475Sodium Thiosulfate PentahydrateHCID 85247Trimethylsilyl iodideHCID 59127168(S)-3-hydroxy-5-(1-methoxypropan-2-yloxy)-N-(5-methylpyrazin-2-yl)benzamide

Product 1

HCID 591271143-hydroxy-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}-N-(5-methylpyrazin-2-yl)benzamideYield 65.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Trimethylsilyl iodide (6.06 mL, 42.75 mmol) was added to a solution of 3-hydroxy-5-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-N-(5-methylpyrazin-2-yl)benzamide (2.71 g, 8.55 mmol) in dry acetonitrile (150 mL) and stirred for 24 hours. Methanol (30 mL) was added to quench the reaction and stirred for 10 minutes. 10% w/v Aqueous sodium thiosulfate pentahydrate (20 mL) was added to the mixture and the organic solvents removed in vacuo. The residue was brought to pH5 with 1M hydrochloric acid and ethyl acetate (80 mL) added. A yellow solid (1.4 g) was separated by filtration. The aqueous filtrate was reextracted into ethyl acetate (2×80 mL) and the combined organic layers dried (MgSO4), filtered and the solvents removed in vacuo. This residue was combined with the yellow solid obtained above and purified by column chromatography, eluting with 5% to 10% methanol in DCM, to give the title compound (1.70 g)

Workup

  1. customto quench
  2. customthe reaction
  3. stirringstirred for 10 minutes
  4. additionwas added to the mixture
  5. customthe organic solvents removed in vacuo
  6. additionadded
  7. customA yellow solid (1.4 g) was separated by filtration
  8. dry with materialthe combined organic layers dried (MgSO4)
  9. filtrationfiltered
  10. customthe solvents removed in vacuo
  11. customobtained above and
  12. custompurified by column chromatography
  13. washeluting with 5% to 10% methanol in DCM

Sources & evidence

ORD record
ord-43cfaf40748848a8a06877856d83de7a
Source dataset
uspto-grants-2010_01
Patent number
US07642263B2

Reaction notes

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