Hydrochloric Acid → HCID 42260557, compound

HRID 534825Notes

Reaction equation

HRID 534825 reaction equation
[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C@H:5]([C:13]([O:15]C)=[O:14])[CH2:4][CH2:3]1.[OH-].[Na+].Cl>CO>[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C@H:5]([C:13]([OH:15])=[O:14])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 42260998Methyl 5-oxo-1-phenylprolinate

Product 1

HCID 42260557HCID 42260557, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 5-oxo-1-phenylprolinate (3.50 g, 15.96 mmol) in methanol (200 mL) was added 1 M NaOH solution (40 mL). After being stirred at room temperature for 2 h, the reaction mixture was acidified with 1 M HCl solution and the mixture was concentrated under reduced pressure. The resulting residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting light yellow solid was triturated with hexane to give the title compound (2.47 g, 75%) as a light yellow solid.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customThe resulting residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting light yellow solid was triturated with hexane

Sources & evidence

ORD record
ord-ede6d568e05b42aeba5680c2487120a6
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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