Sodium Chloride → HCID 46244897, compound

HRID 1689574Notes

Reaction equation

HRID 1689574 reaction equation
[C:1]([O:9][CH2:10][CH:11]1[S:15][CH2:14][CH2:13][O:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(=O)(O)(O)O.P([O-])([O-])([O-])=O.CC(CCC[C@H]([C@@H]1[C@]2(C)[C@H]([C@H]3[C@H](CC2)[C@]2(C)C(C[C@H](CC2)O)=CC3)CC1)C)C.[OH-].[Na+].[Cl-].[Na+]>C(#N)C>[C:1]([O:9][CH2:10][C@H:11]1[S:15][CH2:14][CH2:13][O:12]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[OH:9][CH2:10][C@@H:11]1[S:15][CH2:14][CH2:13][O:12]1

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 5997CholesterolHCID 14798Sodium HydroxideHCID 110640761,3-Oxathiolane-2-methanol, 2-benzoate2×HCID 21872022Phosphoric acid phosphate

Product 2

HCID 46244897HCID 46244897, compoundHCID 469280421,3-Oxathiolane-2-methanol, 2-benzoate, (2R)-

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
4 °C

Procedure

(+/−)-2-(Benzoyloxymethyl)-1,3-oxathiolane (0.71 mmol, 160 mg) was dissolved in acetonitrile (0.6 mL) in a 25-mL round-bottomed flask. A 0.1 M phosphoric acid-phosphate buffer solution (15 mL) adjusted to pH 7.0 was added to the reaction followed by 21 units of cholesterol esterase from bovine pancreas (Sigma #C3766). The reaction was stirred at approximately 4° C. for a period of up to 24 h while maintaining the pH of the reaction media at pH 7.0 with 1 M sodium hydroxide solution. The progress of the reaction may be monitored by gas chromatography for disappearance of the (+/)-2-(benzoyloxymethyl)-1,3-oxathiolane and/or by chiral HPLC for enantiomeric enrichment. When the reaction had proceeded to about 50% conversion, the mixture was saturated with sodium chloride and extracted with methyl tert-butyl ether (5×5 mL). Concentration of the extracts afforded a crude product that was purified by silica gel chromatography to give 2(R)-(benzoyloxymethyl)-1,3-oxathiolane (68 mg) and 2(S)-(hydroxymethyl)-1,3-oxathiolane (38 mg).

Workup

  1. additionwas added to the reaction
  2. temperaturewhile maintaining
  3. customThe progress of the reaction
  4. extractionextracted with methyl tert-butyl ether (5×5 mL)
  5. customConcentration of the extracts afforded a crude product that
  6. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-3116738c12dc4eca8c53481f288dc7b9
Source dataset
uspto-grants-2012_04
Patent number
US08153416B2

Reaction notes

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