Water → HCID 18652161, compound

HRID 1586749Notes

Reaction equation

HRID 1586749 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([OH:12])[CH2:9][C@H:8]1[CH2:13][N:14]1[C:21]2[N:17]([N:18]=[CH:19][CH:20]=2)[CH:16]=[CH:15]1)=[O:6])[CH:2]=[CH2:3].[CH3:22][S:23](Cl)(=[O:25])=[O:24].O>C(OCC)(=O)C.C(N(CC)CC)C>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][S:23]([CH3:22])(=[O:25])=[O:24])[CH2:9][C@H:8]1[CH2:13][N:14]1[C:21]2[N:17]([N:18]=[CH:19][CH:20]=2)[CH:16]=[CH:15]1)=[O:6])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 57171953HCID 57171953, compound

Product 1

HCID 18652161HCID 18652161, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of (2S,4R)-1-allyloxycarbonyl-4-hydroxy-2-(imidazo[1,2-b]pyrazol-1-yl)methylpyrrolidine (3.16 g) in a mixture of ethyl acetate (60 ml) and triethylamine (2.27 ml) was dropwise added a solution of methanesulfonyl chloride (1.18 ml) in ethyl acetate (5 ml) with stirring under ice-cooling. The mixture was stirred at the same temperature for 1 hour. To the reaction mixture was added water (50 ml) with stirring and the organic layer was separated. The organic layer was washed in turn with saturated aqueous sodium chloride, saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo to give a residue. The residue was chromatographed on silica gel (60 g) eluting with a mixture of dichloromethane and acetone (2:1, V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4R)-1-allyloxycarbonyl -2-(imidazo[1,2-b]pyrazol-1-yl)methyl-4-methanesulfonyloxypyrrolidine (3.06 g).

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at the same temperature for 1 hour
  3. stirringwith stirring
  4. customthe organic layer was separated
  5. washThe organic layer was washed in turn with saturated aqueous sodium chloride, saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated in vacuo
  8. customto give a residue
  9. customThe residue was chromatographed on silica gel (60 g)
  10. washeluting with a mixture of dichloromethane and acetone (2:1, V/V)
  11. additionThe fractions containing the desired compound
  12. customwere collected
  13. customevaporated in vacuo

Sources & evidence

ORD record
ord-0e5f57c98e1b4db2aa4966697ae5bdbb
Source dataset
uspto-grants-1993_06
Patent number
US05215983

Reaction notes

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