Sulfuric Acid → HCID 25259510, compound

HRID 494585Notes

Reaction equation

HRID 494585 reaction equation
OC[C@@H](N[C:11](=[O:26])[C@:12]([CH3:25])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:13][CH2:14][C:15]([CH3:18])([CH3:17])[CH3:16])C1C=CC=CC=1.S(=O)(=O)(O)[OH:28]>O1CCOCC1>[CH3:25][C@@:12]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)([CH2:13][CH2:14][C:15]([CH3:16])([CH3:17])[CH3:18])[C:11]([OH:26])=[O:28]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 25259508HCID 25259508, compound

Product 1

HCID 25259510HCID 25259510, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of Example 48A (4.48 g, 12.7 mmol) in 1,4-dioxane (60 mL) was added 4 M sulfuric acid (60 mL) and the reaction was stirred at reflux for 48 hours. The solution was concentrated in vacuo, dissolved in 1 N NaOH (250 mL), and washed with hexane (200 mL). The aqueous layer was acidified to pH 1 with 6 N HCl and extracted with ethyl acetate (3×200 mL). The combined ethyl acetate layers were dried over sodium sulfate, filtered, and concentrated in vacuo to give a clear oil (2.66 g, 90%). 1H NMR (300 MHz, CDCl3): δ ppm 0.86 (s, 9H) 1.09 (m, 2H) 1.56 (s, 3H) 1.99 (m, 2H) 7.33 (m, 5H).

Workup

  1. temperatureat reflux for 48 hours
  2. concentrationThe solution was concentrated in vacuo
  3. dissolutiondissolved in 1 N NaOH (250 mL)
  4. washwashed with hexane (200 mL)
  5. extractionextracted with ethyl acetate (3×200 mL)
  6. dry with materialThe combined ethyl acetate layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5620c4a953f747fbb28844c37d1e5546
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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