Sulfuric Acid → HCID 68874543, compound

HRID 494499Notes

Reaction equation

HRID 494499 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]([CH3:26])([CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])[C:9](N[C@H](C2C=CC=CC=2)CO)=[O:10])=[CH:4][CH:3]=1.S(=O)(=O)(O)[OH:28]>O1CCOCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@:8]([CH3:26])([CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])[C:9]([OH:10])=[O:28])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 68871587HCID 68871587, compound

Product 1

HCID 68874543HCID 68874543, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of the product of Example 22D (6.15 g, 17.2 mmol) in dioxane (100 mL) was treated with 4 M sulfuric acid solution (100 mL), and the mixture was warmed at reflux for 48 h. The solution was cooled and extracted with dichloromethane (3×). The combined organic layers were dried (Na2SO4) and concentrated in vacuo to afford the title compound (4.16 g, 100%) as an amber oil. 1H NMR (300 MHz, CDCl3): δ 0.86 (t, J=6.43 Hz, 6 H) 1.05 (m, 2 H) 1.51 (m, 4 H) 1.96 (m, 2 H) 7.02 (m, 2 H) 7.34 (m, 2 H). Specific Rotation: [□]D−10.6°(c 2.15, EtOH).

Workup

  1. temperaturethe mixture was warmed
  2. temperatureat reflux for 48 h
  3. temperatureThe solution was cooled
  4. extractionextracted with dichloromethane (3×)
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-47b18629e9e14879aa1360f73c52f65a
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

Loading…