Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Glycine ethyl ester, hydrochloride | HCID 2723640 | — |
| Reactant | (5-Fluoro-2-nitrophenyl)methanol | HCID 12016493 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 21285525 | HCID 21285525 | — |
Reaction Steps
1.8 g (10.7 mmol) of 5-fluoro-2-nitrobenzyl alcohol was dissolved in 20 ml of dichloromethane. 0.9 ml (12.8 mmol) of methanesulfonyl chloride and 2.2 ml (16.1 mmol) of triethylamine were added to the obtained solution, and they were stirred at room temperature for 2 hours. After the treatment with dichloromethane as the extracting solvent by an ordinary method, the obtained crude product was dissolved in 20 ml of ethanol. 1.79 g (12.8 mmol) of glycine ethyl ester hydrochloride and 1.35 g (16.1 mmol) of sodium hydrogencarbonate were added to the obtained solution, and they were stirred at 70° C. for 6 hours. The solvent was evaporated. After the extraction with ethyl acetate, the extract was washed with 1 N hydrochloric acid. The obtained aqueous layer was made basic with 1 N sodium hydroxide. After the extraction with ethyl acetate, the obtained organic layer was washed with saturated aqueous sodium chloride solution and then dried. The solvent was evaporated to obtain the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06825191B2 |
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| Source dataset | uspto-grants-2004_11 |
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| ORD ID | ord-6f2202b40e22458694dd4c2dd4b15479 |
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| Source note | uspto-grants-2004_11 |
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