1,2-Dichloroethane → HCID 86679444, compound

HRID 1776494Notes

Reaction equation

HRID 1776494 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[NH2:6].[CH2:12]([O:19][C:20](=[O:25])[CH2:21][C:22](O)=[O:23])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(Cl)CCl>CN(C1C=CN=CC=1)C.CN(C=O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:6][C:22](=[O:23])[CH2:21][C:20]([O:19][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:25])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

7

Reactant 3

HCID 111,2-DichloroethaneHCID 227703,4-DimethoxyanilineHCID 1816593-(Benzyloxy)-3-oxopropanoic acid

Product 1

HCID 86679444HCID 86679444, compoundYield 49.4%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3,4-dimethoxyaniline (500 mg, 3.26 mmol), 3-(benzyloxy)-3-oxopropanoic acid (1268 mg, 6.53 mmol), DMAP (798 mg, 6.53 mmol), and EDC (1877 mg, 9.79 mmol) were dissolved in DMF (7 ml). The reaction was stirred at RT for 4 hours to achieve completion. The reaction mixture was diluted with water, and the precipitate was washed with water, dissolved in EtOAc and extracted with HCl 1N, Na2CO3 sat. sol. and brine. The organic phase was dried over Na2SO4 and concentrated under vacuum to give benzyl 3-(3,4-dimethoxyphenylamino)-3-oxopropanoate (530 mg, 49.3% yield).

Workup

  1. washthe precipitate was washed with water
  2. dissolutiondissolved in EtOAc
  3. extractionextracted with HCl 1N, Na2CO3 sat. sol. and brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-8d9cb1c9a79d438e8e6d5ed04585c0c7
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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