Sulfuric Acid → (S)-4-hydroxy-3-methanesulfonyl hydroxybutyric acid

HRID 1977497Notes

Reaction equation

HRID 1977497 reaction equation
[CH3:1][S:2]([CH:5]1[CH2:10][O:9][C:7](=[O:8])[C@@H:6]1[OH:11])(=[O:4])=[O:3].S(=O)(=O)(O)[OH:13]>>[OH:9][CH2:10][CH:5]([S:2]([CH3:1])(=[O:4])=[O:3])[C@@H:6]([OH:11])[C:7]([OH:13])=[O:8]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 86756702(S)-3-methanesulfonyl hydroxybutyrolactone

Product 1

HCID 86756701(S)-4-hydroxy-3-methanesulfonyl hydroxybutyric acid

Conditions

Temperature
50 °C

Procedure

(S)-3-methanesulfonyl hydroxybutyrolactone (1.0 g, 5.6 mmol), D2O (10 ml), and the concentrated sulfuric acid (0.0549 g, 0.56 mmol) were placed in a 25 ml reactor and stirred at 50° C. for 3 hours. The reacting solution was cooled to room temperature and extracted with dichloromethane (10 ml) twice to recover the unreacted (S)-3-methanesulfonyl hydroxybutyrolactone. The presence of the target (S)-4-hydroxy-3-methanesulfonyl hydroxybutyric acid in a pure form in the D2O layer was confirmed by nuclear magnetic resonance.

Workup

  1. temperatureThe reacting solution was cooled to room temperature
  2. extractionextracted with dichloromethane (10 ml) twice
  3. customto recover the unreacted (S)-3-methanesulfonyl hydroxybutyrolactone

Sources & evidence

ORD record
ord-6c4d0ae92bbc4f4399d033835c900eac
Source dataset
uspto-grants-2001_05
Patent number
US06232478B1

Reaction notes

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