Water → HCID 86756319, compound

HRID 568273Notes

Reaction equation

HRID 568273 reaction equation
[C:1]([O-:4])(=[S:3])[CH3:2].[K+].[CH2:6]([O:9][C:10]([N:12]1[C@H:16]([CH:17]([OH:26])[C:18]2[S:22][C:21]3=[CH:23][N:24]=[CH:25][N:20]3[CH:19]=2)[CH2:15][C@@H:14](OS(C)(=O)=O)[CH2:13]1)=[O:11])[CH:7]=[CH2:8].O>CN(C=O)C>[C:1]([S:3][C@H:14]1[CH2:15][C@@H:16]([CH:17]([OH:26])[C:18]2[S:22][C:21]3=[CH:23][N:24]=[CH:25][N:20]3[CH:19]=2)[N:12]([C:10]([O:9][CH2:6][CH:7]=[CH2:8])=[O:11])[CH2:13]1)(=[O:4])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 23670855Potassium ethanethioateHCID 86756320HCID 86756320, compound

Product 1

HCID 86756319HCID 86756319, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium thioacetate (204 mg) is added to a solution of 236.9 mg of (3R,5S)-1-allyloxycarbonyl-3-methanesulfonyloxy-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-2-yl)methyl]pyrrolidine (a diastereomer mixture) in 10 ml of DMF, and the mixture is stirred under an argon stream a 70° C. for 5 hr. The reaction solution is cooled, water is added thereto, and the mixture is extracted three times with ethyl acetate. The organic layer is washed once with saturated saline, dried over anhydrous magnesium sulfate and filtered, and the solvent is removed by evaporation under reduced pressure. The resultant crude product is purified by column chromatography on silica gel (hexane:acetone=1:1) to give 136.4 mg of the title compound (a diastereomer mixture) as a brown oil.

Workup

  1. temperatureThe reaction solution is cooled
  2. extractionthe mixture is extracted three times with ethyl acetate
  3. washThe organic layer is washed once with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent is removed by evaporation under reduced pressure
  7. customThe resultant crude product is purified by column chromatography on silica gel (hexane:acetone=1:1)

Sources & evidence

ORD record
ord-d78015984cab4043bb09e2efe925b837
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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