Sulfuric Acid → HCID 178460592, compound

HRID 1685809Notes

Reaction equation

HRID 1685809 reaction equation
[O:1]=[C:2]1[CH2:6][S:5][CH2:4][CH:3]1[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:18])[C:15]([OH:17])=[S:16])=[CH:10][CH:9]=1.[BH4-].[Na+].S(=O)(=O)(O)O>O1CCCC1>[OH:1][CH:2]1[CH2:6][S:5][CH2:4][CH:3]1[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:18])[C:15]([OH:17])=[S:16])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 4311764Sodium borohydrideHCID 178460591HCID 178460591, compound

Product 1

HCID 178460592HCID 178460592, compoundYield 15.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[4-(4-Oxothiolan-3-ylmethyl)phenyl]thiopropionic acid (100 mg) obtained in Example 11 was dissolved in tetrahydrofuran (5.0 ml), and to the solution was added sodium borohydride (16.2 mg) under ice cooling, and then the reaction mixture was stirred at room temperature for 4 hours. After completion of the reaction, to the reaction mixture was added 0.5 M aqueous sulfuric acid, and the reaction mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to give the compounds of Example 12-A (pale brown oil, 16 mg, 15.9%) and Example 12-B (colorless oil, 12 mg, 11.9%).

Workup

  1. customAfter completion of the reaction
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-c22f74e337914bfbb451f082f1d1bb07
Source dataset
uspto-grants-2012_04
Patent number
US08148421B2

Reaction notes

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