Potassium ethanethioate → (3S,5S)-3-Acetylthio-1-allyloxycarbonyl-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-3-yl)methyl]pyrrolidine

HRID 568264Notes

Reaction equation

HRID 568264 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[N:19]3[CH:25]=[N:24][CH:23]=[C:20]3[S:21][CH:22]=2)[CH2:15][C@@H:14](OS(C)(=O)=O)[CH2:13]1)=[O:11])[CH:7]=[CH2:8]>CN(C=O)C.C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:1]([S:3][C@H:14]1[CH2:15][C@@H:16]([CH:17]([OH:26])[C:18]2[N:19]3[CH:25]=[N:24][CH:23]=[C:20]3[S:21][CH:22]=2)[N:12]([C:10]([O:9][CH2:6][CH:7]=[CH2:8])=[O:11])[CH2:13]1)(=[O:4])[CH3:2]

Participants

6

Reactant 2

HCID 23670855Potassium ethanethioateHCID 86756315(3R,5S)-1-allyloxycarbonyl-5-[1-hydroxy-(imidazo[5,1-b]thiazol-3-yl)methyl]-3-methanesulfonyloxypyrrolidine

Product 1

HCID 86756316(3S,5S)-3-Acetylthio-1-allyloxycarbonyl-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-3-yl)methyl]pyrrolidineYield 72.7%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

Potassium thioacetate (134 mg) is added to a solution of 314 mg of (3R,5S)-1-allyloxycarbonyl-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-3-yl)methyl]-3-methanesulfonyloxypyrrolidine (stereoisomer A) in a mixture of 4 ml of dry DMF and 2 ml of dry toluene, and the mixture is stirred in an argon atmosphere at a bath temperature of 70° C. for 22 hr. The mixture is diluted with 60 ml of ethyl acetate and washed twice with semi-saturated saline, and the organic layer is dried over magnesium sulfate and filtered. The solvent is removed by evaporation under reduced pressure, and the residue is dried under reduced pressure by means of a vacuum pump. The dark red oil is purified by flash column chromatography on silica gel (ethyl acetate) to give 217 mg of the title compound as a slightly red amorphous material.

Workup

  1. washwashed twice with semi-saturated saline
  2. dry with materialthe organic layer is dried over magnesium sulfate
  3. filtrationfiltered
  4. customThe solvent is removed by evaporation under reduced pressure
  5. customthe residue is dried under reduced pressure by means of a vacuum pump
  6. customThe dark red oil is purified by flash column chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-70c402430e374d75a6466e5f07f64ece
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

Loading…