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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Methoxyacetic acid is an endogenous metabolite.
4.5
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| CAS No. : | 625-45-6 |
| Formula : | C3H6O3 |
| M.W : | 90.07 |
| SMILES Code : | COCC(O)=O |
| English Name : | 2-Methoxyacetic acid |
| MDL No. : | MFCD00004308 |
| InChI Key : | RMIODHQZRUFFFF-UHFFFAOYSA-N |
| Pubchem ID : | 12251 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 69% | With hydrogenchloride In lithium hydroxide monohydrate for 16h; Reflux; | |
| 44.3% | With hydrogenchloride In lithium hydroxide monohydrate for 18h; Reflux; | |
| With hydrogenchloride |
| at 140 - 150℃; | ||
| With hydrogenchloride In lithium hydroxide monohydrate at 20℃; for 3 - 4h; Reflux; Green chemistry; | General procedure General procedure: To a stirred mixture of alcohol (1, 10 mmol) and KBr (0.24 g, 2 mmol), in water (5 ml) at room temperature was added iodosobenzene (4.84 g, 22 mmol) in parts and stirred overnight. To the reaction mixture was then added 4N HCl (5 ml) followed by OPD (1.08 g, 10 mmol). The reaction mixture was refluxed for 3-4 h and was cooled to room temperature. It was then basified with NH4OH and extracted with dichloromethane (2 x 10 ml), the organic layer was dried over Na2SO4 . The solvent was removed by distillation and the residue was triturated with pet ether to remove iodobenzene to give solid product 3, which was recrystallized from aqueous ethanol. |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 80% | With ammonium persulfate; silver nitrate In water; acetonitrile |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With sodium tetrahydroborate 1.) benzene, 0 deg C - 10 deg C, 2.) toluene, reflux, 2 h; Multistep reaction; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Stage #1: 2-methoxyacetic acid; (3aS,4S,6R,6aR)-6-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbaldehyde; 4-(benzyloxy)phenyl isocyanide With Rink amide resin In pyridine; methanol; N,N-dimethyl-formamide at 20℃; for 48h; Stage #2: With hydrogenchloride In methanol at 20℃; for 0.5h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 95% | With dimesitylammonium pentafluorobenzenesulfonate In n-heptane at 80℃; for 4h; | |
| 93% | With dimesitylammonium pentafluorobenzenesulfonate In n-heptane at 80℃; for 10h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With dmap; dicyclohexyl-carbodiimide In DMF (N,N-dimethyl-formamide) at 20℃; for 72h; | 148 Reference Example 148 To a solution of 5-(2-chlorophenyl)cyclohexane-1,3-dione (1.0 g), 4-dimethylaminopyridine (0.82 g) and methoxyacetic acid (0.73 g) in dimethylformamide (40 ml) was added dicyclohexylcarbodiimide (1.0 g), and the mixture was stirred at room temperature for 3 days. Under reduced pressure, the solvent was evaporated, and to the residue was added ethyl acetate. Insoluble materials were filtered off, and the organic layer was extracted with 1N sodium hydroxide solution. To the aqueous layer was added 1N hydrochloric acid to make the solution acidic, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated to give 5-(2-chlorophenyl)-2-(1-hydroxy-2-methoxyethylidene)cyclohexane-1,3-dione (0.86 g) as oil. 1H-NMR(CDCl3) δ: 2.44-3.2 (5H,m), 3.51 (3H,s), 3.78-3.98 (1H,m), 4.76 (2H,s), 7.1-7.44 (4H,m). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 73% | Stage #1: 5-bromo-3-nitrobenzene-1,2-diamine; 2-methoxyacetic acid at 110℃; for 16h; Stage #2: With sodium hydroxide In water at 0℃; | I.L L. 6-bromo-2-methoxymethyl-4-nitro-1(3) H-benzimidazole A suspension of 1 g (4.3 MMOL) 5-bromo-3-nitro-1, 2-phenylenediamine in 4 mi methoxyacetic acid was heated to 110 B0;C for 16 h. The mixture was poured into icewater, neutralized with 6N aqueous sodium hydroxide and extracted with DICHLOROMETHANE. The organic layer was separated, dried over anhydrous magnesium sulphate and evaporated. Purification of the residue by crystallization from ethyl acetate and activated charcoal yielded 0.9 g (73 %) of the title compound as a colourless solid (m. p. 173 B0;C). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 56 EXAMPLE 56 EXAMPLE 56 Addition of phosphonyl chloride to a mixture of thiosemicarbazide and methoxyacetic acid at 60°-95° and working up of the product yields 5-amino-2-methoxymethyl-(1,3,4)-thiadiazole, m.p. 177°-179° (from water). | ||
| 86 EXAMPLE 86 EXAMPLE 86 Addition of phosphonyl chloride to a mixture of thiosemicarbazide and methoxyacetic acid at 60°-95° and working up of the product yields 5-amino-2-methoxymethyl-(1,3,4)-thiadiazole, m.p. 177°-179° (from water). |