Potassium Carbonate → HCID 68426419, compound

HRID 642313Notes

Reaction equation

HRID 642313 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([N:11]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:8][C:7]=1[CH2:25]Br)=[O:5])[CH3:2].[CH2:27]([O:29][C:30](=[O:44])[CH2:31][NH:32][CH2:33][C:34]1[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][C:35]=1[O:42][CH3:43])[CH3:28].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([N:11]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:8][C:7]=1[CH2:25][N:32]([CH2:33][C:34]1[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][C:35]=1[O:42][CH3:43])[CH2:31][C:30]([O:29][CH2:27][CH3:28])=[O:44])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 19895532Ethyl 2-(2,4-dimethoxybenzylamino)acetateHCID 68426696HCID 68426696, compound

Product 1

HCID 68426419HCID 68426419, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-bromomethyl-2-(tert-butoxycarbonyl-phenyl-amino)-thiazole-5-carboxylic acid ethyl ester (451 mg, 1.02 mmol), (2,4-dimethoxy-benzylamino)-acetic acid ethyl ester (260 mg, 1.02 mmol) and potassium carbonate (213 g, 1.54 mmol) in anhydrous dimethylformamide (4 mL) was stirred at room temperature for 18 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 white solid (562 mg): MS: (+) m/z 614.13 (M+1).

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-6ec10b9dc274470197d6258bbb400b2d
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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