Hydrochloric Acid → HCID 15086221, compound

HRID 1613992Notes

Reaction equation

HRID 1613992 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH2:13][C@H:12]1[CH2:21][N:22]1[CH:26]=[CH:25][N:24]=[CH:23]1)=[O:10])[C:2]1C=CC=C[CH:3]=1.Cl.[H][H].ClC(OCC=C)=O.[OH-].[Na+].[Cl-].[Na+]>[Pd].O1CCCC1.O.C(OCC)(=O)C.CO>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][S:17]([CH3:20])(=[O:18])=[O:19])[CH2:13][C@H:12]1[CH2:21][N:22]1[CH:26]=[CH:25][N:24]=[CH:23]1)=[O:10])[CH:2]=[CH2:3]

Participants

12

Reactant 6

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 18052Allyl chloroformateHCID 15086214HCID 15086214, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15086221HCID 15086221, compoundYield 78.4%

Reagents, catalysts & solvents 5

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (2S,4R)-1-benzyloxycarbonyl-2-(imidazol-1-yl)methyl-4-methanesulfonyloxypyrrolidine (8.60 g), conc. hydrochloric acid (1.76 ml), methanol (80 ml) and 10% palladium on carbon (50% wet) (4.50 g) was stirred for 6 hours under atmospheric pressure of hydrogen residue. The residue was dissolved in a mixture of tetrahydrofuran (22 ml) and water (22 ml). To the solution was added dropwise allyl chloroformate (2.5 ml) under ice-cooling, keeping pH 9-10 with 4N sodium hydroxide and then the mixture was stirred at the same condition for 30 minutes. To the reaction mixture were added sodium chloride (1.0 g) and ethyl acetate (10 ml). The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo to give (2S,4R)-1-allyloxycarbonyl-2-(imidazol-1-yl)methyl-4-methanesulfonyloxypyrrolidine (5.85 g).

Workup

  1. temperaturecooling
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-3e49b4bc2ba24f5a898b4c4fb7d94352
Source dataset
uspto-grants-1993_03
Patent number
US05194624

Reaction notes

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