Potassium Carbonate → 4-{[(2,4-Dimethoxy-benzyl)-ethoxycarbonylmethyl-amino]-methyl}-2-phenyl-thiazole-5-carboxylic acid ethyl ester

HRID 642277Notes

Reaction equation

HRID 642277 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH2:17]Br)=[O:5])[CH3:2].[CH2:19]([O:21][C:22](=[O:36])[CH2:23][NH:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:27]=1[O:34][CH3:35])[CH3:20].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH2:17][N:24]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:27]=1[O:34][CH3:35])[CH2:23][C:22]([O:21][CH2:19][CH3:20])=[O:36])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12736369Ethyl 4-(bromomethyl)-2-phenyl-1,3-thiazole-5-carboxylateHCID 19895532Ethyl 2-(2,4-dimethoxybenzylamino)acetate

Product 1

HCID 684272284-{[(2,4-Dimethoxy-benzyl)-ethoxycarbonylmethyl-amino]-methyl}-2-phenyl-thiazole-5-carboxylic acid ethyl esterYield 70.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-bromomethyl-2-phenyl-thiazole-5-carboxylic acid ethyl ester (5.29 g, 16.3 mmol), (2,4-dimethoxy-benzylamino)-acetic acid ethyl ester (4.12 g, 16.3 mmol) and potassium carbonate (3.37 g, 24.4 mmol) in anhydrous dimethylformamide (50 mL) was stirred at room temperature for 16 h before it was quenched with water, extracted with ethyl acetate. The organic layer was washed with water, brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes to give the title compound as a yellow oil (5.72 g): MS: (+) m/z 499.0 (M+H+), 521.2 (M+Na+).

Workup

  1. customwas quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes

Sources & evidence

ORD record
ord-679c6d58713044399b1beac66ada98ca
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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