Sulfuric Acid → HCID 25259509, compound

HRID 494563Notes

Reaction equation

HRID 494563 reaction equation
OC[C@@H](N[C:11](=[O:25])[C@@:12]([CH3:24])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])C1C=CC=CC=1.S(=O)(=O)(O)[OH:27]>O1CCOCC1>[CH3:24][C@@:12]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([CH2:13][CH2:14][CH:15]([CH3:16])[CH3:17])[C:11]([OH:25])=[O:27]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 25259506HCID 25259506, compound

Product 1

HCID 25259509HCID 25259509, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of Example 40A (4.26 g, 12.55 mmol) in 1,4-dioxane (15 mL) was added 4M sulfuric acid (15 mL) and the reaction was stirred at reflux for 48 hours. The solution was concentrated in vacuo and partitioned between water and methylene chloride. The methylene chloride layer was dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with hexane, 10% ethyl acetate in hexane, and 20% ethyl acetate in hexane to give the title compound (2.02 g, 73%). 1H NMR (300 MHz, CDCl3): δ ppm 0.88 (m, 6H) 1.09 (m, 2H) 1.52 (m, 4H) 1.99 (m, 2H) 7.35 (m, 5H).

Workup

  1. temperatureat reflux for 48 hours
  2. concentrationThe solution was concentrated in vacuo
  3. custompartitioned between water and methylene chloride
  4. dry with materialThe methylene chloride layer was dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica gel eluting with hexane, 10% ethyl acetate in hexane, and 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-8271bfae8b02424a97e4179463d3c9e8
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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