Acetic Acid → HCID 19347983, compound

HRID 1637203Notes

Reaction equation

HRID 1637203 reaction equation
[OH:1]O.O.[OH:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12][C:13]1[C:14]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]3[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=3)=[CH:23][C:15]=2[S:16][C:17]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19].Cl.[C:36](O)(=[O:38])[CH3:37]>>[CH3:37][C:36]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12]([C:13]1[C:14]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]3[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=3)=[CH:23][C:15]=2[S:16][C:17]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:1])=[O:38]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 9868451HCID 9868451, compound

Product 1

HCID 19347983HCID 19347983, compound

Conditions

Temperature
100 °C

Procedure

Hydrogen peroxide in water (0.23 ml of 30% w/v, 2.05 mmol) was added to a mixture of ethyl 3-[2-(hydroxymethyl)phenylsulfanyl]-6-(3-pyridylmethoxy)benzo[b]thiophene-2-carboxylate (Example 13, 770 mg, 1.71 mmol) in acetic acid (5 ml), and 2M aqueous hydrochloric acid (0.8 ml). The mixture was heated to 100° C. for 3 hours, cooled, and the solvents removed under reduced pressure. The residue was partitioned between ethyl acetate and aqueous sodium bicarbonate solution, and the organic layer was separated, dried (magnesium sulfate) and concentrated under vacuo. The residue was flash chromatographed on silica gel using a mixture of 75% ethyl acetate and 25% hexane as eluant, to give the title compound as a colourless solid (500 mg).

Workup

  1. temperaturecooled
  2. customthe solvents removed under reduced pressure
  3. customThe residue was partitioned between ethyl acetate and aqueous sodium bicarbonate solution
  4. customthe organic layer was separated
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated under vacuo
  7. customchromatographed on silica gel using
  8. additiona mixture of 75% ethyl acetate and 25% hexane as eluant

Sources & evidence

ORD record
ord-f45a17136376499e81f4b93cbe75a9ae
Source dataset
uspto-grants-2000_03
Patent number
US06040309

Reaction notes

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