Potassium ethanethioate → HCID 53805923, compound

HRID 903435Notes

Reaction equation

HRID 903435 reaction equation
[C:1]([O-:4])(=[S:3])[CH3:2].[K+].[C:6]([CH:14](Br)[CH:15]([CH3:26])[C:16]([N:18]1[CH2:25][CH2:24][CH2:23][C@H:19]1[C:20]([OH:22])=[O:21])=[O:17])(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(O)C>[C:1]([S:3][CH:14]([C:6](=[O:13])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH:15]([CH3:26])[C:16]([N:18]1[CH2:25][CH2:24][CH2:23][C@H:19]1[C:20]([OH:22])=[O:21])=[O:17])(=[O:4])[CH3:2]

Participants

4

Reactant 2

HCID 23670855Potassium ethanethioate2×HCID 54223915HCID 54223915, compound

Product 1

HCID 53805923HCID 53805923, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a suspension of 0.47 g of potassium thioacetate in 10 ml. of ethanol is added 1.25 g. of 1-(3-benzoyl-3-bromo-2-methylpropionyl)-L-proline (Example 11, 3-bromo derivative of isomer A). The mixture is stirred for 18 hours, the solvent is removed in vacuo and the residue is partitioned between dichloromethane and water. The organic layer is washed with water, then sodium chloride solution and dried over magnesium sulfate. The solvent is removed in vacuo giving a yellow glass which is dissolved in 10 ml. of ethanol. A 0.47 g. portion of potassium thioacetate is added and the above procedure is repeated giving a yellow glass. This glass is purified by chromatography on a silica gel column with ethyl acetate-hexane-acetic acid (75:25:2) giving 0.28 g. of the desired product as a yellow glass.

Workup

  1. customthe solvent is removed in vacuo
  2. customthe residue is partitioned between dichloromethane and water
  3. washThe organic layer is washed with water
  4. dry with materialsodium chloride solution and dried over magnesium sulfate
  5. customThe solvent is removed in vacuo
  6. customgiving a yellow glass which
  7. dissolutionis dissolved in 10 ml
  8. customthe above procedure is repeated giving a yellow glass
  9. customThis glass is purified by chromatography on a silica gel column with ethyl acetate-hexane-acetic acid (75:25:2)
  10. customgiving 0.28 g

Sources & evidence

ORD record
ord-ad6c7a6cfc5845cdbd97dd8c0fb12c91
Source dataset
uspto-grants-1980_10
Patent number
US04226775

Reaction notes

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