Potassium ethanethioate → HCID 86749918, compound

HRID 864511Notes

Reaction equation

HRID 864511 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:10][C@H:9]3[C@@H:11]([O:30][C:31](=[O:33])[CH3:32])[C@@H:12]([O:26][C:27](=[O:29])[CH3:28])[C@@H:13](OS(C4C=CC(C)=CC=4)(=O)=O)[O:14][C@H:8]3[N:7]([CH2:34][CH2:35][N:36]([CH2:39][CH3:40])[CH2:37][CH3:38])[C:6]=2[CH:41]=1.[C:42]([O-:45])(=[S:44])[CH3:43].[K+]>CC(C)=O>[C:42]([S:44][C@H:13]1[O:14][C@@H:8]2[C@@H:9]([S:10][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:41][C:6]=3[N:7]2[CH2:34][CH2:35][N:36]([CH2:37][CH3:38])[CH2:39][CH3:40])[C@@H:11]([O:30][C:31](=[O:33])[CH3:32])[C@H:12]1[O:26][C:27](=[O:29])[CH3:28])(=[O:45])[CH3:43]

Participants

4

Reactant 2

HCID 23670855Potassium ethanethioateHCID 86749916(2R, 3R, 4S, 4aS, 10aR)-8-chloro-3, 4-diacetoxy-10-(2-diethylaminoethyl)-2-(4-methylphenylsulfonyloxy)-2, 3, 4, 4a, 10, 10a-hexahydropyrano [3, 2-b] [1, 4] benzothiazine

Product 1

HCID 86749918HCID 86749918, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To the solution of 2.0 g of the compound (36) obtained in Example 35 in 100 ml of acetone, 1.0 g of potassium thioacetate was added, and the mixture was heated with refluxing for 6.5 hours. The solvent was removed under reduced pressure, and the residue was dissolved in ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to obtain 1.65 g (yield 96.8% ) of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperaturewith refluxing for 6.5 hours
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-fd8b095a20c04b00982a1f3983b569cf
Source dataset
uspto-grants-1996_10
Patent number
US05563137

Reaction notes

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