Ethyl Acetate → HCID 70220260, compound

HRID 568283Notes

Reaction equation

HRID 568283 reaction equation
CC(C)([O-])C.[K+].Cl.[Cl-].[S:9]1[CH:13]=[C:12]([CH2:14][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[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][Si](C(C)(C)C)(C)C)[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:12]2[N:11]3[CH:34]=[N:35][CH:36]=[C:10]3[S:9][CH:13]=2)[CH2:46][C@@H:45]([OH:50])[CH2:44]1)=[O:42])[CH:38]=[CH2:39]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 21262435HCID 21262435, compoundHCID 22870383(2S,4R)-1-allyloxycarbonyl-4-t-butyldimethylsilyloxy-2-formylpyrrolidineHCID 23665647Potassium tert-butoxide

Product 1

HCID 70220260HCID 70220260, compoundYield 53.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Potassium-t-butoxide (1.95 g) is added to a solution of 4.09 g of (imidazo[5,1-b]thiazol-3-yl)methyltriphenylphosphonium chloride hydrochloride in 15 ml of THF and 15 ml of DMSO under ice cooling. The mixture is stirred for 2 hr, a solution of 2.9 g of (3R,5S)-1-allyloxycarbonyl-3-t-butyldimethylsilyloxy-5-formylpyrrolidine in 15 ml of THF is added thereto, and the mixture is stirred under ice cooling for 2 hr. Ethyl acetate is added to the reaction mixture, 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 dissolved in 80 ml of methanol, 3.5 ml of a 5 N aqueous hydrochloric acid solution is added to the solution, and the mixture is stirred at room temperature for 12 hr. The mixture is neutralized with a 5 N aqueous sodium hydroxide solution, dichloromethane is added thereto, and the mixture is successively washed with water and saturated saline and dried over magnesium sulfate. The solvent is removed by evaporation, and the residue is purified by column chromatography on silica gel to give 1.48 g of (3R,5S)-1-allyloxycarbonyl-3-hydroxy-5-[2-(imidazo[5,1-b]thiazol-3-yl)ethenyl]pyrrolidine.

Workup

  1. stirringthe mixture is stirred under ice cooling for 2 hr
  2. washthe mixture is successively washed with dilute hydrochloric acid and saturated saline
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent is removed by evaporation
  5. dissolutionthe residue is dissolved in 80 ml of methanol
  6. addition3.5 ml of a 5 N aqueous hydrochloric acid solution is added to the solution
  7. stirringthe mixture is stirred at room temperature for 12 hr
  8. additionis added
  9. washthe mixture is successively washed with water and saturated saline
  10. dry with materialdried over magnesium sulfate
  11. customThe solvent is removed by evaporation
  12. customthe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-c5c589d2d4ce47c1a18988fde21566cd
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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