Water → Methyl 4-{4-[(2-ethoxy-2-oxoethyl)(methyl)amino]-2-formylbutyl}benzoate

HRID 2243290Notes

Reaction equation

HRID 2243290 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([CH:15]=[O:16])[CH2:12][CH2:13]Br)=[CH:6][CH:5]=1.Cl.[NH:19]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH3:20].C(=O)(O)[O-].[Na+].O>C(#N)C>[CH2:25]([O:24][C:22](=[O:23])[CH2:21][N:19]([CH3:20])[CH2:13][CH2:12][CH:11]([CH:15]=[O:16])[CH2:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([O:2][CH3:1])=[O:17])=[CH:5][CH:6]=1)[CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 171173Ethyl N-methylaminoacetate hydrochlorideHCID 516892Sodium BicarbonateHCID 17958613Methyl 4-(4-bromo-2-formylbutyl)benzoate

Product 1

HCID 59210615Methyl 4-{4-[(2-ethoxy-2-oxoethyl)(methyl)amino]-2-formylbutyl}benzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.500 g (1.67 mmol) of methyl-4-(4-bromo-2-formylbutyl)benzoate from Ex. VIII, 0.257 g (1.67 mmol) of ethyl sarcosinate hydrochloride and 0.309 g (3.68 mmol) of sodium bicarbonate in 10 ml of acetonitrile are heated at reflux for 1 hour. The reaction mixture is cooled, 50 ml of water are added and the mixture is extracted repeatedly with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution and dried over magnesium sulfate, and the solvent is distilled off under reduced pressure. The crude product is purified by chromatography on silica gel (0.04-0.063 nm) using methylene chloride/methanol 100:3 as mobile phase.

Workup

  1. temperatureat reflux for 1 hour
  2. temperatureThe reaction mixture is cooled
  3. extractionthe mixture is extracted repeatedly with ethyl acetate
  4. washThe combined organic phases are washed with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. distillationthe solvent is distilled off under reduced pressure
  7. customThe crude product is purified by chromatography on silica gel (0.04-0.063 nm)

Sources & evidence

ORD record
ord-f51aed66484647c9b754d6bad5a2a61e
Source dataset
uspto-grants-2010_03
Patent number
US07674825B2

Reaction notes

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