Water → HCID 90281932, compound

HRID 1497512Notes

Reaction equation

HRID 1497512 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].Cl.[NH2:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:22]([O:21][C:19](=[O:20])[CH2:18][NH:17][CH2:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 22456708tert-Butyl 3-(chloromethyl)benzoate

Product 1

HCID 90281932HCID 90281932, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl 3-(chloromethyl)benzoate (25.3 g) in N,N-dimethylformamide (250 mL) were added tert-butyl glycinate hydrochloride (37.4 g) and potassium carbonate (61.7 g), followed by stirring at 60° C. overnight. To the reaction suspension was added water, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain tert-butyl 3-{[(2-tert-butoxy-2-oxoethyl)amino]methyl}benzoate (23.0 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous sodium chloride solution, then dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-5dde00b7edd044d4bb4066d1ec51fe1c
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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