Benzoyl chloride → HCID 66936364, compound

HRID 1366527Notes

Reaction equation

HRID 1366527 reaction equation
[CH3:1][C:2]([C:11]([O:13][CH3:14])=[O:12])([CH3:10])[NH:3][CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7].C([O-])(O)=O.[Na+].[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl.O>[CH3:10][C:2]([C:11]([O:13][CH3:14])=[O:12])([CH3:1])[N:3]([CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7])[C:20]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:27]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 516892Sodium BicarbonateHCID 13601736N-(3-Methoxy-3-oxopropyl)-2-methylalanine methyl ester

Product 1

HCID 66936364HCID 66936364, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 21908982Water methylene chlorideSolvent

Procedure

To a mixture of methyl 2-methyl-N-[3-(methyloxy)-3-oxopropyl]alaninate (11.71 g, 57.62 mmol) in 1:1 DCM-water (300 mL) was added NaHCO3 (9.68 g, 115.2 mmol) followed by benzoyl chloride (7.02 mL, 60.48 mmol). The mixture was vigorously stirred overnight, and the phases were then separated. The organic phase was dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (35% EtOAc in hexanes) to give methyl 2-methyl-N-[3-(methyloxy)-3-oxopropyl]-N-(phenylcarbonyl)alaninate (3.6787 g, 21% yield) as a colorless oil. LCMS: (M+H)+: 308.1.

Workup

  1. customthe phases were then separated
  2. dry with materialThe organic phase was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography (35% EtOAc in hexanes)

Sources & evidence

ORD record
ord-5cee7f025c1b40e1a37faa883739ee64
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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