Hydrochloric Acid → 2-(3-Carboxymethyl-4-nitrophenyl)propionic acid

HRID 1873228Notes

Reaction equation

HRID 1873228 reaction equation
[OH-].[Na+].Cl.C([CH:7]([C:29]([O:31]C)=[O:30])[C:8]1[CH:9]=[C:10]([C:17](C)([C:23](OCC)=O)[C:18]([O:20]CC)=[O:19])[CH:11]=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15])(=O)C>CO>[C:29]([CH2:7][C:8]1[CH:9]=[C:10]([CH:17]([CH3:23])[C:18]([OH:20])=[O:19])[CH:11]=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15])([OH:31])=[O:30]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10960547HCID 10960547, compound2×

Product 1

HCID 186886652-(3-Carboxymethyl-4-nitrophenyl)propionic acidYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In methanol (1 mL) was dissolved diethyl 2-[3-[acetyl(methoxycarbonyl)methyl]-4-nitrophenyl]-2-methylmalonate (obtained in (1) above, 50.9 mg, 0.124 mmol.). The resulting solution was stirred for 15 hours at room temperature after addition of 2M aqueous sodium hydroxide solution (1.5 mL, 3 mmol.). The reaction mixture was then stirred at 60° C. for 3 hours after addition of 6M hydrochloric acid (1 mL, 3 mmol.). The mixture was cooled and extracted with ethyl acetate. The ethyl acetate portion was washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The dried organic portion was concentrated and purified by silica gel column chromatography (Wako Gel C-200, available from Wako Jyunyaku Industry Co., Ltd., hexane/ethyl acetate/acetic acid=7/3/1, v/v/v), to give 20.3 mg (yield: 65%) of the desired compound.

Workup

  1. stirringThe reaction mixture was then stirred at 60° C. for 3 hours
  2. temperatureThe mixture was cooled
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate portion was washed with an aqueous saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe dried organic portion was concentrated
  7. custompurified by silica gel column chromatography (Wako Gel C-200, available from Wako Jyunyaku Industry Co., Ltd., hexane/ethyl acetate/acetic acid=7/3/1, v/v/v)

Sources & evidence

ORD record
ord-d07d8f6a78884e579c8af124579d115d
Source dataset
uspto-grants-2000_08
Patent number
US06111115

Reaction notes

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