Hydrochloric Acid → HCID 15086221, compound

HRID 1613994Notes

Reaction equation

HRID 1613994 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

Conditions

Temperature
72.5 °C

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-f3eb65867d194392a0bc83c09b55f0d2
Source dataset
uspto-grants-1993_03
Patent number
US05194624

Reaction notes

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