4-Chlorobenzaldehyde → HCID 21019793, compound

HRID 1745393Notes

Reaction equation

HRID 1745393 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:11])[C@H:5]([CH2:7][CH2:8][S:9][CH3:10])[NH2:6].C(=O)([O-])[O-].[Na+].[Na+].[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1>O>[CH3:2][O:3][C:4](=[O:11])[CH:5]([N:6]=[CH:23][C:22]1[CH:25]=[CH:26][C:19]([Cl:18])=[CH:20][CH:21]=1)[CH2:7][CH2:8][S:9][CH3:10]

Participants

5

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 10340Sodium CarbonateHCID 11435579L-Methionine, methyl ester, hydrochloride

Product 1

HCID 21019793HCID 21019793, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of L-methionine methyl ester hydrochloride (2 g, 10.0 mmol) and sodium carbonate (1.06 g, 10.0 mmol) in water (46 mL) was added p-chlorobenzaldehyde (1.4 g, 10.0 mmol). The resulting mixture was stirred at 40° C. for 45 minutes then 17 h at room temperature. The white cloudy solution was extracted with dichloromethane (3×50 mL). The organic phase was washed with water (2×50 mL), dried over anhydrous magnesium sulfate and concentrated in vacuo to yield the title compound 2.6 g (91%) which was used in next step with out further purification.

Workup

  1. custom17 h
  2. customat room temperature
  3. extractionThe white cloudy solution was extracted with dichloromethane (3×50 mL)
  4. washThe organic phase was washed with water (2×50 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-64eee39f25044cff99188e4036ef315d
Source dataset
uspto-grants-2006_03
Patent number
US07019019B2

Reaction notes

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