Sulfuric Acid → HCID 25259510, compound

HRID 2224905Notes

Reaction equation

HRID 2224905 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, 9 H) 1.09 m, 2 H) 1.56 (s, 3 H) 1.99 m, 2 H) 7.33 m, 5 H).

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-65e61d88ffa0441fac6311f022152c72
Source dataset
uspto-grants-2008_05
Patent number
US07378414B2

Reaction notes

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