Sodium Hydroxide → 3-(4-(Methylthio)phenylamino)-3-oxopropanoic acid

HRID 1776492Notes

Reaction equation

HRID 1776492 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:22])[CH2:11][C:12]([O:14]CC2C=CC=CC=2)=[O:13])=[CH:5][CH:4]=1.[OH-].[Na+]>CO.Cl>[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:22])[CH2:11][C:12]([OH:14])=[O:13])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86679443Benzyl 3-(4-(methylthio)phenylamino)-3-oxopropanoate

Product 1

HCID 622307273-(4-(Methylthio)phenylamino)-3-oxopropanoic acidYield 84%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

Benzyl 3-(4-(methylthio)phenylamino)-3-oxopropanoate (150 mg, 0.476 mmol) was dissolved in MeOH (1.5 ml). NaOH 1M (500 μl) was added, and the reaction was stirred at 40° C. for 2 hours to achieve completion. The reaction mixture was diluted with HCl 1N and extracted with EtOAc. The organic phase was washed with HCl 1N and brine, dried over Na2SO4 and concentrated under vacuum to give 3-(4-(methylthio)phenylamino)-3-oxopropanoic acid (90 mg, 84% yield).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed with HCl 1N and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-dd585cbeb5314c6481e7a600d75e718f
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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