Triethylamine → (3R,5S)-1-allyloxycarbonyl-5-[1-hydroxy-(imidazo[5,1-b]thiazol-3-yl)methyl]-3-methanesulfonyloxypyrrolidine

HRID 568263Notes

Reaction equation

HRID 568263 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[CH2:13]([O:16][C:17]([N:19]1[C@H:23]([CH:24]([OH:33])[C:25]2[N:26]3[CH:32]=[N:31][CH:30]=[C:27]3[S:28][CH:29]=2)[CH2:22][C@@H:21]([OH:34])[CH2:20]1)=[O:18])[CH:14]=[CH2:15].C(=O)([O-])O.[Na+]>C1COCC1>[CH2:13]([O:16][C:17]([N:19]1[C@H:23]([CH:24]([OH:33])[C:25]2[N:26]3[CH:32]=[N:31][CH:30]=[C:27]3[S:28][CH:29]=2)[CH2:22][C@@H:21]([O:34][S:9]([CH3:8])(=[O:11])=[O:10])[CH2:20]1)=[O:18])[CH:14]=[CH2:15]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 70220671(3R,5S)-1-allyloxycarbonyl-3-hydroxy-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-3-yl)methyl]pyrrolidine

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (0.25 ml) and 0.12 ml of methanesulfonyl chloride are successively added to a solution of 457 mg of crude (3R,5S)-1-allyloxycarbonyl-3-hydroxy-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-3-yl)methyl]pyrrolidine (stereoisomer A) in 12 ml of dry THF in an argon atmosphere at 3° C., and the mixture is stirred in this state for 30 min. A 5% aqueous sodium hydrogencarbonate solution (30 ml) is added thereto, and the mixture is extracted with 100 ml of ethyl acetate. The organic layer is washed with saturated saline, dried over magnesium sulfate, and filtered, and the solvent is removed by evaporation under reduced pressure to give a slightly cloudy orange brown oil. This oil is purified by flash column chromatography on silica gel (ethyl acetate:methanol=92:8) to give 344 mg of crude (3R,5S)-1-allyloxycarbonyl-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-3-yl)methyl]-3-methanesulfonyloxypyrrolidine (stereoisomer A) as a milky white amorphous material.

Workup

  1. extractionthe mixture is extracted with 100 ml of ethyl acetate
  2. washThe organic layer is washed with saturated saline
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent is removed by evaporation under reduced pressure
  6. customto give a slightly cloudy orange brown oil
  7. customThis oil is purified by flash column chromatography on silica gel (ethyl acetate:methanol=92:8)

Sources & evidence

ORD record
ord-80c06c16148c4cbca59339b7b2597ac1
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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