Potassium ethanethioate → HCID 53709393, compound

HRID 903439Notes

Reaction equation

HRID 903439 reaction equation
[C:1]([O-:4])(=[S:3])[CH3:2].[K+].Br[CH:7]([C:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:8][C:9]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])=[O:10]>C(O)C>[C:1]([S:3][CH:7]([C:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:8][C:9]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])=[O:10])(=[O:4])[CH3:2]

Participants

4

Reactant 2

HCID 23670855Potassium ethanethioateHCID 53886994HCID 53886994, compound

Product 1

HCID 53709393HCID 53709393, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred mixture of 1.25 g. of potassium thioacetate in 20 ml. of ethanol is added a solution of 3.54 g. of 1-(3-bromo-3-benzoylpropionyl)-L-proline (Example 20) in 20 ml. of ethanol. The mixture is stirred at room temperature for 2 hours. The mixture is concentrated to dryness under vacuum and the residue partitioned between dichloromethane and water. The dichloromethane layer is washed with saturated sodium chloride solution and dried over magnesium sulfate. The solvent is removed under vacuum to give 2.9 g. of product as a glass. A 2.3 g. sample is chromatographed over silica gel with solvent system, ethyl acetate-hexane-acetic acid (75:25:2) to give 1.07 g. of product as a pale yellow glass.

Workup

  1. additionTo a stirred mixture of 1.25 g
  2. concentrationThe mixture is concentrated to dryness under vacuum
  3. customthe residue partitioned between dichloromethane and water
  4. washThe dichloromethane layer is washed with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent is removed under vacuum
  7. customto give 2.9 g
  8. customsample is chromatographed over silica gel with solvent system, ethyl acetate-hexane-acetic acid (75:25:2)
  9. customto give 1.07 g

Sources & evidence

ORD record
ord-1206500e52c54adaa64f39b1b69623d0
Source dataset
uspto-grants-1980_10
Patent number
US04226775

Reaction notes

Loading…