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

HRID 642384Notes

Reaction equation

HRID 642384 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([Br:11])=[N:8][C:7]=1[CH2:12]Br)=[O:5])[CH3:2].[CH2:14]([O:16][C:17](=[O:31])[CH2:18][NH:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=1[O:29][CH3:30])[CH3:15].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([Br:11])=[N:8][C:7]=1[CH2:12][N:19]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=1[O:29][CH3:30])[CH2:18][C:17]([O:16][CH2:14][CH3:15])=[O:31])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 19895532Ethyl 2-(2,4-dimethoxybenzylamino)acetateHCID 68428140Ethyl 2-bromo-4-(bromomethyl)thiazole-5-carboxylate

Product 1

HCID 684264542-Bromo-4-{[(2,4-dimethoxy-benzyl)-ethoxycarbonylmethyl-amino]-methyl}-thiazole-5-carboxylic acid ethyl esterYield 57.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Bromo-4-bromomethyl-thiazole-5-carboxylic acid ethyl ester (22.1 g, 67.3 mmol) was dissolved in 169 mL of dry N,N-dimethylformamide. N-(2,4-dimethoxy-benzyl)glycine ethyl ester (17.1 g, 67.3 mmol) and potassium carbonate (10.2 g, 74.0 mmol) were added and the reaction was stirred at room temperature for 18 h. The reaction mixture was diluted with ethyl acetate and washed with water and brine. The organic fraction was dried over anhydrous sodium sulfate, and concentrated. The crude product was purified by flash chromatography eluting from silica gel with a gradient of 0-70% ethyl acetate in hexanes to produce 19.5 g of a light yellow solid. MS: (+) m/z 501.1 (M+1).

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic fraction was dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe crude product was purified by flash chromatography
  5. washeluting from silica gel with a gradient of 0-70% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-527270feef9b4bb4a78be8587fe5724e
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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