Ethyl Acetate → HCID 86756328, compound

HRID 568287Notes

Reaction equation

HRID 568287 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]=[CH:18][C:19]2[S:23][C:22]3=[CH:24][N:25]=[CH:26][N:21]3[CH:20]=2)[CH2:15][C@@H:14](OS(C)(=O)=O)[CH2:13]1)=[O:11])[CH:7]=[CH2:8].C(OCC)(=O)C>CN(C=O)C>[C:1]([S:3][C@H:14]1[CH2:15][C@@H:16]([CH:17]=[CH:18][C:19]2[S:23][C:22]3=[CH:24][N:25]=[CH:26][N:21]3[CH:20]=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 8857Ethyl AcetateHCID 23670855Potassium ethanethioateHCID 86756327HCID 86756327, compound

Product 1

HCID 86756328HCID 86756328, compoundYield 57.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Potassium thioacetate (0.22 g) is added to a solution of 1.07 g of (3R,5S)-1-allyloxycarbonyl-3-methane sulfonyloxy-5-[2-(imidazo[5,1-b]thiazol-2-yl)vinyl]pyrrolidine (a mixture of geometrical isomers) in 5 ml of DMF, and the mixture is stirred at 70° C. for 4 hr. Ethyl acetate is added to the reaction mixture, and the mixture is successively washed with water and a saturated aqueous sodium hydrogencarbonate solution, and saturated saline and dried over magnesium sulfate. The solvent is removed by evaporation. The residue is purified by column chromatography on silica gel to give 0.42 g of the title compound.

Workup

  1. washthe mixture is successively washed with water
  2. dry with materiala saturated aqueous sodium hydrogencarbonate solution, and saturated saline and dried over magnesium sulfate
  3. customThe solvent is removed by evaporation
  4. customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-fe358b7dbbbf45858bd2e6bb110f8a10
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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