Citric Acid → HCID 57758716, compound

HRID 1176713Notes

Reaction equation

HRID 1176713 reaction equation
[H-].[Na+].[CH3:3][C@:4]1([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:8](=[CH2:9])[C:7](=[O:10])[N:6]([C@@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:12])[CH2:5]1.[I-].[CH3:27][S+](C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CS(C)=O.O>[CH3:3][C@:4]1([C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[C:8]2([CH2:27][CH2:9]2)[C:7](=[O:10])[N:6]([C@@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:12])[CH2:5]1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodideHCID 57931876HCID 57931876, compound

Product 1

HCID 57758716HCID 57758716, compoundYield 60.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Sodium hydride (60% in oil, 76.1 mg, 1.74 mmol) and a solution of tert-butyl (3S)-3-methyl-4-methylene-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate (500 mg, 1.59 mmol) in dimethylsulfoxide (24 mL) were added sequentially to a solution of trimethylsulfonium iodide (401 mg, 1.82 mmol) in dimethylsulfoxide (8 mL), and the mixture was stirred at 90° C. for 30 minutes. 10% Aqueous citric acid (32 mL) and water (96 mL) were added to the reaction mixture at room temperature, followed by extraction with ethyl acetate (200 mL×2). The obtained organic layer was washed sequentially with water (100 mL) and saturated brine (100 mL). The organic layer was dried over sodium sulfate anhydrate. After filtration, the filtrate was evaporated to dryness under reduced pressure. The residue was purified through silica gel column chromatography (eluent; hexane:ethyl acetate 3:1 to 2:1), to thereby yield the title compound as colorless crystals (315 mg, 60.3%). 1H-NMR and IR spectral data of this product were found to coincide with those obtained in Example 5.

Workup

  1. extractionfollowed by extraction with ethyl acetate (200 mL×2)
  2. washThe obtained organic layer was washed sequentially with water (100 mL) and saturated brine (100 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate anhydrate
  4. filtrationAfter filtration
  5. customthe filtrate was evaporated to dryness under reduced pressure
  6. customThe residue was purified through silica gel column chromatography (eluent; hexane:ethyl acetate 3:1 to 2:1)

Sources & evidence

ORD record
ord-669e7f4ad94d4e5399e5ed5807d10088
Source dataset
uspto-grants-2010_11
Patent number
US07842818B2

Reaction notes

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