HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → 2-Bromo-4-{[(2,4-dimethoxy-benzyl)-ethoxycarbonylmethyl-amino]-methyl}-thiazole-5-carboxylic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Ethyl 2-(2,4-dimethoxybenzylamino)acetate | HCID 19895532 | — |
| Reactant | Ethyl 2-bromo-4-(bromomethyl)thiazole-5-carboxylate | HCID 68428140 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-Bromo-4-{[(2,4-dimethoxy-benzyl)-ethoxycarbonylmethyl-amino]-methyl}-thiazole-5-carboxylic acid ethyl ester | HCID 68426454 | 96.3% |
Reaction Steps
A mixture of 2-bromo-4-bromomethyl-thiazole-5-carboxylic acid ethyl ester (3.57 g, 10.91 mmole), (2,4-dimethoxy-benzylamino)-acetic acid ethyl ester (2.76 g, 10.91 mmole) and potassium carbonate (2.26 g, 16.36 mmole) in anhydrous dimethylformamide (25 ml) was stirred at room temperature for 17 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 (5.27 g): MS: (+) m/z 523.11, 525.04 (M+Na+, 79Br/81Br)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07696223B2 |
| Source dataset | uspto-grants-2010_04 |
| ORD ID | ord-fae7eef44ad0426f9267d514938571af |
| Source note | uspto-grants-2010_04 |