Hydrochloric Acid → HCID 70222219, compound

HRID 568275Notes

Reaction equation

HRID 568275 reaction equation
Cl.[CH2:2]([O:5][C:6]([N:8]1[C@H:12]([CH2:13][C:14]2[N:15]3[CH:21]=[N:20][CH:19]=[C:16]3[S:17][CH:18]=2)[CH2:11][C@@H:10]([O:22][Si](C(C)(C)C)(C)C)[CH2:9]1)=[O:7])[CH:3]=[CH2:4].C(OCC)(=O)C.C(=O)([O-])O.[Na+]>C(#N)C.O>[CH2:2]([O:5][C:6]([N:8]1[C@H:12]([CH2:13][C:14]2[N:15]3[CH:21]=[N:20][CH:19]=[C:16]3[S:17][CH:18]=2)[CH2:11][C@@H:10]([OH:22])[CH2:9]1)=[O:7])[CH:3]=[CH2:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 20639566HCID 20639566, compound

Product 1

HCID 70222219HCID 70222219, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Concentrated hydrochloric acid (0.75 ml) is added dropwise to a solution of 732 mg of (3R,5R)-1-allyloxycarbonyl-3-t-butyldimethylsilyloxy-5-(imidazo[5,1-b]thiazol-3-yl)methylpyrrolidine in 15 ml of dry acetonitrile under ice cooling, and the mixture is stirred at that temperature for 30 min. The reaction solution is diluted wit 50 ml of ethyl acetate, water is added thereto, and the mixture is rendered weakly alkaline by addition of a saturated aqueous sodium hydrogencarbonate solution and extracted three times with ethyl acetate. The organic layer is washed once with saturated saline, dried over anhydrous magnesium sulfate, and filtered, and the solvent is removed by evaporation under reduced pressure to give a crude product of (3R,5R)-1-allyloxycarbonyl-3-hydroxy-5-(imidazo[5,1-b]thiazol-3-yl)methylpyrrolidine. Triethylamine (0.41 ml) and 0.23 ml of methanesulfonyl chloride are successively added to a solution of this compound in 3 ml of dichloromethane under an argon stream under ice cooling, and the mixture is stirred at that temperature for 2 hr. Water is added to the reaction solution, and the mixture is extracted three times with dichloromethane. The organic layer is washed twice with saturated saline, dried over anhydrous magnesium sulfate, and filtered, and the solvent is removed by evaporation under reduced pressure to give a crude product which is then purified by column chromatography on silica gel (ethyl acetate) to give 428.2 mg of (3R,5R)-1-allyloxycarbonyl-5-(imidazo[5,1-b]thiazol-3-yl)methyl-3-methanesulfonyloxypyrrolidine as a colorless oil.

Workup

  1. additionis added
  2. extractionextracted three times with ethyl acetate
  3. washThe organic layer is washed once with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent is removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-d66accaa93664a4bb1649cfd727ff78f
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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