Methanol → HCID 18511990, compound

HRID 1370859Notes

Reaction equation

HRID 1370859 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:11][CH2:12][C:13]1[CH:30]=[CH:29][C:16]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[CH:20][CH:19]=2)=[CH:15][CH:14]=1.OS(O)(=O)=O.[CH3:36]O>C(OCC)(=O)C>[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:11][CH2:12][C:13]1[CH:30]=[CH:29][C:16]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([O:28][CH3:36])=[O:27])=[CH:20][CH:19]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 18512364HCID 18512364, compound

Product 1

HCID 18511990HCID 18511990, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The product from Example 76B (9.78 g, 24.1 mmoles) in MeOH (24 mL) was treated with concentrated H2SO4 (1 mL) and heated at reflux overnight. Reaction cooled and quenched with saturated NaHCO3. Reaction mixture diluted with ethyl acetate, washed with H2O, brine, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, 20% ethyl acetate:hexanes) to provide the title compound. MS (ESI−) m/z 419 (M−H)−.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. customReaction
  4. temperaturecooled
  5. customquenched with saturated NaHCO3
  6. customReaction mixture
  7. washwashed with H2O, brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationthe filtrate concentrated under reduced pressure
  11. customThe residue was purified by flash chromatography (silica gel, 20% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-2ea934dc3b314803a24b71713b37fbe9
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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