Potassium ethanethioate → HCID 54147731, compound

HRID 978832Notes

Reaction equation

HRID 978832 reaction equation
C([O:4][C@@H:5]1[NH:8][C:7](=O)[C@H:6]1[NH:10][C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=O)C.[C:30]([O-:33])(=[S:32])[CH3:31].[K+]>CO.O>[C:30]([S:32][C@H:7]1[NH:8][C:5](=[O:4])[C@H:6]1[NH:10][C:11]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)(=[O:33])[CH3:31]

Participants

5

Reactant 2

HCID 23670855Potassium ethanethioateHCID 53918863HCID 53918863, compound

Product 1

HCID 54147731HCID 54147731, compoundYield 26.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 0.7 g of (3S,4S)-4-acetoxy-3-tritylamino-2-oxoazetidine in 10 ml of methanol is added a solution of 0.25 g of potassium thioacetate in 2 ml of water. The mixture is stirred for 30 minutes at 55°-60° C. Methanol is distilled off under reduced pressure. To the residue is added ethyl acetate, followed by washing with water, drying and concentration under reduced pressure. The residue is purified on a silica-gel column (ethyl acetate:n-hexane=1:1) to give 0.195 g of (3R,4R)-4-acetylthio-3-tritylamino-2-oxoazetidine

Workup

  1. distillationMethanol is distilled off under reduced pressure
  2. additionTo the residue is added ethyl acetate
  3. washby washing with water
  4. customdrying
  5. concentrationconcentration under reduced pressure
  6. customThe residue is purified on a silica-gel column (ethyl acetate:n-hexane=1:1)

Sources & evidence

ORD record
ord-217d25a1a4bd4afb9ffcd488dcc64025
Source dataset
uspto-grants-1987_05
Patent number
US04665067

Reaction notes

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