Sulfuric Acid → HCID 25260202, compound

HRID 494589Notes

Reaction equation

HRID 494589 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 25259507HCID 25259507, compound

Product 1

HCID 25260202HCID 25260202, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of Example 49A (3.78 g, 10.7 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 (2.47 g, 98%). 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-33aa2d30d05e4c8d866d521e4f3f43ba
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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