Dimethyl Sulfoxide → HCID 86756330, compound

HRID 568290Notes

Reaction equation

HRID 568290 reaction equation
CC(C)([O-])C.[K+].[Cl-].[S:8]1[CH:12]=[CH:11][N:10]2[C:13]([CH2:16][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=[N:14][CH:15]=[C:9]12.[CH2:36]([O:39][C:40]([N:42]1[C@H:46]([CH:47]=O)[CH2:45][C@@H:44]([O:49][Si](C(C)(C)C)(C)C)[CH2:43]1)=[O:41])[CH:37]=[CH2:38].C(OCC)(=[O:59])C.C[S:64]([CH3:66])=[O:65]>C1COCC1>[CH2:36]([O:39][C:40]([N:42]1[C@H:46]([CH:47]=[CH:16][C:13]2[N:10]3[C:9]([S:8][CH:12]=[CH:11]3)=[CH:15][N:14]=2)[CH2:45][C@@H:44]([O:49][S:64]([CH3:66])(=[O:59])=[O:65])[CH2:43]1)=[O:41])[CH:37]=[CH2:38]

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 8857Ethyl AcetateHCID 21262400HCID 21262400, compoundHCID 22870383(2S,4R)-1-allyloxycarbonyl-4-t-butyldimethylsilyloxy-2-formylpyrrolidineHCID 23665647Potassium tert-butoxide

Product 1

HCID 86756330HCID 86756330, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Potassium t-butoxide (0.11 g) is added to a solution of 0.44 g of (imidazo[5,1-b]thiazol-5-yl)methyltriphenylphosphonium chloride in 2 ml of THF and 2 ml of dimethyl sulfoxide under ice cooling. The mixture is stirred at that temperature for one hr, and a solution of 0.28 g of (3R,5S)-1-allyloxycarbonyl-3-t-butyldimethylsilyloxy-5-formylpyrrolidine in 2 ml of THF, and the mixture is stirred at that temperature for 2 hr. Ethyl acetate is added to the reaction mixture, and the mixture is successively washed with dilute hydrochloric acid, a saturated aqueous sodium hydrogencarbonate solution and saturated saline and dried over anhydrous magnesium sulfate. The solvent is removed by evaporation, and the residue is purified by column chromatography on silica gel (methanol:ethyl acetate=5:95) to give 0.33 g of (3R,5S)-1-allyloxycarbonyl-5-[2-(imidazo[5,1-b]thiazol-5-yl)ethenyl]-3-methanesulfonyloxypyrrolidine (a mixture of geometrical isomers).

Workup

  1. washthe mixture is successively washed with dilute hydrochloric acid
  2. dry with materiala saturated aqueous sodium hydrogencarbonate solution and saturated saline and dried over anhydrous magnesium sulfate
  3. customThe solvent is removed by evaporation
  4. customthe residue is purified by column chromatography on silica gel (methanol:ethyl acetate=5:95)

Sources & evidence

ORD record
ord-926aefcf4dd04b8a8d2dcd8d37ed5b94
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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