関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Water | HCID 962 | — |
| 反応物 | Potassium Carbonate | HCID 11430 | — |
| 反応物 | tert-Butyl N-(2-bromoethyl)carbamate | HCID 4103526 | — |
| 反応物 | Methyl 3,4-Dihydroxyphenylacetate | HCID 11008556 | — |
| 溶媒 | Hydrochloric Acid | HCID 313 | — |
| 溶媒 | Methanol | HCID 887 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 溶媒 | Sodium Hydroxide | HCID 14798 | — |
| 生成物 | 2-(3,4-Bis(2-(tert-butoxycarbonylamino)ethoxy)phenyl)acetic acid | HCID 86725281 | — |
反応手順
To methyl 2-(3,4-dihydroxyphenyl)acetate (1.0 g) in DMF (10 mL) was added tert-butyl 2-bromoethylcarbamate (2.7 g) and K2CO3 (1.7 g). The resulting reaction mixture was stirred at 60° C. overnight. Water was added and the aqueous phase extracted with EtOAc. The organic phase was then dried and concentrated. The residue was purified by flash chromatography. The product was obtained as a mixture of mono- and bis-alkylation. The mixture was then dissolved in MeOH and THF (10 mL, 1:1) and IN NaOH was added. The resulting reaction mixture was stirred at room temperature overnight. IN HCl was added to acidify the solution. The aqueous phase was extracted with EtOAc (3×). The organic phases were combined, dried and concentrated. The title product was obtained by reverse phase chromatography purification (0.5 g).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 特許番号 | US09403850B2 |
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| 出典データセット | uspto-grants-2016_08 |
|---|
| ORD ID | ord-c12e81b672324999a5c61d59ee958931 |
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| 出典メモ | uspto-grants-2016_08 |
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