4-Sulfanylidene-1,3-thiazolidin-2-one → HCID 178518187, compound

HRID 1620756Notes

Reaction equation

HRID 1620756 reaction equation
[NH2:1][C@H:2]1[C@H:7]([OH:8])[CH2:6][CH2:5][O:4][CH2:3]1.S=[C:10]1[CH2:14][S:13][C:12](=[O:15])[NH:11]1>C(O)C>[O:15]=[C:12]1[N:11]=[C:10]([NH:1][C@H:2]2[C@H:7]([OH:8])[CH2:6][CH2:5][O:4][CH2:3]2)[CH2:14][S:13]1

Participants

4

Reactant 2

HCID 15395954-Sulfanylidene-1,3-thiazolidin-2-oneHCID 72207589(3R,4R)-3-Aminotetrahydro-2H-pyran-4-ol

Product 1

HCID 178518187HCID 178518187, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-amino-1,5-anhydro-2,4-dideoxy-threo-pentitol (527 mg) in ethanol (100 mL) was added 4-thioxo-1,3-thiazolidin-2-one (590 mg), and the mixture was heated under reflux for 15 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, ethyl acetate) to give the title compound (700 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 15 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (NH, ethyl acetate)

Sources & evidence

ORD record
ord-831048285ab54fbf96293076f12e765d
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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