Hydrochloric Acid → HCID 15086221, compound

HRID 1088634Notes

Reaction equation

HRID 1088634 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH2:9][C@H:8]1[CH2:17]OS(C)(=O)=O)=[O:6])[CH:2]=[CH2:3].[NH:23]1[CH:27]=[CH:26][N:25]=[CH:24]1.O.Cl>C(OCC)(=O)C>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][S:13]([CH3:16])(=[O:14])=[O:15])[CH2:9][C@H:8]1[CH2:17][N:23]1[CH:27]=[CH:26][N:25]=[CH:24]1)=[O:6])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 962WaterHCID 15086220HCID 15086220, compound

Product 1

HCID 15086221HCID 15086221, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of {2S,4R)-1-allyloxycarbonyl-4-methanesulfonyloxy-2-(methanesulfonyloxy)methylpyrrolidine (8.73 g) and imidazole (4.16 g) was stirred at 70°-75° C. for 7 hours. After cooling, the reaction mixture was dissolved in ethyl acetate (30 ml), water (30 ml) and conc. hydrochloric acid (8.0 ml) with stirring. The aqueous layer was separated, adjusted to pH 9.0 with 10% aqueous sodium hydroxide and extracted twice with ethyl acetate (50 ml). The extract was dried over anhydrous magnesium sulfate and evaporated in vacuo to give (2S,4R)-1-allyloxycarbonyl-2-(imidazol-1-yl)methyl-4-methanesulfonyloxypyrrolidine (5.30 g).

Workup

  1. temperatureAfter cooling
  2. customThe aqueous layer was separated
  3. extractionextracted twice with ethyl acetate (50 ml)
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-44fde894461d4225a8bdc8e25e5af299
Source dataset
uspto-grants-1990_10
Patent number
US04963544

Reaction notes

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