Ethyl Acetate → HCID 86756327, compound

HRID 568286Notes

Reaction equation

HRID 568286 reaction equation
CC(C)([O-])C.[K+].Cl.[Cl-].[S:9]1[C:13]([CH2:14][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:12][N:11]2[CH:34]=[N:35][CH:36]=[C:10]12.[CH2:37]([O:40][C:41]([N:43]1[C@H:47]([CH:48]=O)[CH2:46][C@@H:45]([O:50][S:51]([CH3:54])(=[O:53])=[O:52])[CH2:44]1)=[O:42])[CH:38]=[CH2:39].C(OCC)(=O)C>C1COCC1.CS(C)=O>[CH2:37]([O:40][C:41]([N:43]1[C@H:47]([CH:48]=[CH:14][C:13]2[S:9][C:10]3=[CH:36][N:35]=[CH:34][N:11]3[CH:12]=2)[CH2:46][C@@H:45]([O:50][S:51]([CH3:54])(=[O:52])=[O:53])[CH2:44]1)=[O:42])[CH:38]=[CH2:39]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 12018288HCID 12018288, compoundHCID 21262375HCID 21262375, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 86756327HCID 86756327, compoundYield 56.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Potassium t-butoxide (1.06 g) is added to a solution of 2.24 g of (imidazo[5,1-b]thiazol-2-yl)methyltriphenylphosphonium chloride hydrochloride in a mixture of 5 ml of THF and 5 ml of dimethylsulfoxide under ice cooling. The mixture is stirred under ice cooling for 2 hr, a solution of 1.32 g of (3R,5S)-1-allyloxycarbonyl-3-methanesulfonyloxy-5-formylpyrrolidine in 5 ml of THF, and the mixture is stirred under ice cooling for 2 hr. Ethyl acetate is added to the reaction mixture, and the mixture is successively washed with dilute hydrochloric acid 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 1.07 g of (3R,5S)-1-allyloxycarbonyl-3-methanesulfonyloxy-5-[2-(imidazo[5,1-b]thiazol-2-yl)vinyl]pyrrolidine (a mixture of geometrical isomers).

Workup

  1. washthe mixture is successively washed with dilute hydrochloric acid and saturated saline
  2. dry with materialdried 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-a6f79c4015d74a738a2d4c5d59ad5e49
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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