Potassium ethanethioate → HCID 54552710, compound

HRID 903449Notes

Reaction equation

HRID 903449 reaction equation
Br[CH:2]([C:15](=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:3][CH2:4][C:5]([N:7]1[CH2:14][CH2:13][CH2:12][C@H:8]1[C:9]([OH:11])=[O:10])=[O:6].[C:23]([O-:26])(=[S:25])[CH3:24].[K+]>C(O)C>[C:23]([S:25][CH:2]([C:15](=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:3][CH2:4][C:5]([N:7]1[CH2:14][CH2:13][CH2:12][C@H:8]1[C:9]([OH:11])=[O:10])=[O:6])(=[O:26])[CH3:24]

Participants

4

Reactant 2

HCID 23670855Potassium ethanethioateHCID 53902176HCID 53902176, compound

Product 1

HCID 54552710HCID 54552710, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2.0 g. of 1-(4-bromo-4-benzoylbutyryl)-L-proline (Example 42) in 20 ml. of ethanol is added 752 mg. of potassium thioacetate. The mixture is stirred at room temperature for 18 hours, evaporated to dryness and the residue is partitioned between dichloromethane and water. The dichloromethane layer is separated, washed with saline, dried over magnesium sulfate, treated with charcoal and evaporated to a gum. This gum is dissolved in ethyl acetate-hexane-acetic acid (75:25:2) and chromatographed on a 1"×15" silica gel column (100 ml. hold back volume) taking 50 ml. cuts. Cuts 3-6 are combined to give the desired product.

Workup

  1. customevaporated to dryness
  2. customthe residue is partitioned between dichloromethane and water
  3. customThe dichloromethane layer is separated
  4. washwashed with saline
  5. dry with materialdried over magnesium sulfate
  6. additiontreated with charcoal
  7. customevaporated to a gum
  8. dissolutionThis gum is dissolved in ethyl acetate-hexane-acetic acid (75:25:2)
  9. customchromatographed on a 1"×15" silica gel column (100 ml. hold back volume)

Sources & evidence

ORD record
ord-3a5e531d205a48dbb0a942973e3f9dd8
Source dataset
uspto-grants-1980_10
Patent number
US04226775

Reaction notes

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