Sulfuric Acid → (S)-Atrolactic acid

HRID 1942498Notes

Reaction equation

HRID 1942498 reaction equation
[OH:1][C@:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:6])[C:3]([OH:5])=[O:4].C1([C@@H](N)C)C2C(=CC=CC=2)C=CC=1.S(=O)(=O)(O)O>CO>[OH:1][C@:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:6])[C:3]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 67331018HCID 67331018, compound

Product 1

HCID 445144(S)-Atrolactic acidYield 109.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(2S)-2-Hydroxy-2-phenylpropanoic acid-(1S)-1-(1-naphthyl)ethanamine (1:1) (1.54 g) was dissolved in methanol (50 ml), and thereto was slowly added dropwise conc. sulfuric acid (5 ml). After the addition was complete, the mixture was refluxed for 10 hours. The reaction solution was cooled to room temperature, and concentrated under reduced pressure to remove methanol. The residue was dissolved in ethyl acetate, washed with water, a saturated aqueous sodium hydrogen carbonate solution, and a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the title compound (0.83 g).

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was refluxed for 10 hours
  3. concentrationconcentrated under reduced pressure
  4. customto remove methanol
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with water
  7. dry with materiala saturated aqueous sodium hydrogen carbonate solution, and a saturated aqueous sodium chloride solution, dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a0667a4fadcf451795fd148124e5ccc8
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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