HCID 19849033, compound → HCID 19849018, compound

HRID 1608277Notes

Reaction equation

HRID 1608277 reaction equation
[C:1]([O-:4])(=[S:3])[CH3:2].[K+].CC1C=CC(S(O[CH2:17][CH:18]2[CH2:22][S:21][C:20]3([CH2:26][CH2:25][CH:24]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:23]3)[O:19]2)(=O)=O)=CC=1>CC(C)=O>[C:1]([S:3][CH2:17][CH:18]1[CH2:22][S:21][C:20]2([CH2:26][CH2:25][CH:24]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:23]2)[O:19]1)(=[O:4])[CH3:2]

Participants

4

Reactant 2

HCID 19849033HCID 19849033, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 19849018HCID 19849018, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred slurry of potassium thioacetate (1.14 g, 10 mmol) in a solution of the tosylate of Example P (4.15 g, 10 mmol) in acetone (30 ml) is refluxed under nitrogen for 5 hrs. The reaction mixture is filtered and the filtrate is concentrated on a rotary evaporator. The residue is dissolved in ethyl acetate, washed with water and dried over sodium sulfate. The drying agent is filtered, the solvent is removed using the rotary evaporator and the residue is chromatographed on silica gel using mixtures of ethyl acetate and hexane as eluents to give the titled compound.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated on a rotary evaporator
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationThe drying agent is filtered
  7. customthe solvent is removed
  8. customthe rotary evaporator
  9. customthe residue is chromatographed on silica gel using mixtures of ethyl acetate and hexane as eluents

Sources & evidence

ORD record
ord-1534ebca2efe4e4b988c38a85e4e8b1c
Source dataset
uspto-grants-1989_09
Patent number
US04870098

Reaction notes

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