関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Benzylamine | HCID 7504 | — |
| 反応物 | Diisopropylcarbodiimide | HCID 12734 | — |
| 反応物 | 1-Hydroxybenzotriazole | HCID 75771 | — |
| 反応物 | Diisopropylethylamine | HCID 81531 | — |
| 反応物 | Sodium cyanoborohydride | HCID 5003444 | — |
| 反応物 | Trifluoroacetic acid methylene chloride | HCID 21863450 | — |
| 反応物 | Acetic anhydride triethylamine | HCID 21881581 | — |
| 溶媒 | Acetate | HCID 175 | — |
| 溶媒 | dichloromethane N,N-dimethylformamide | HCID 22350042 | — |
| 生成物 | 2-(3-formyl-1H-indol-1-yl)acetic acid | HCID 771465 | — |
反応手順
3-Formylindol-1-ylacetic acid was prepared and coupled to the beads above according to the process of EP 0 801 083 A2 (Estep et al.) using diisopropyl carbodiimide, N,N-diisopropylethylamine, and N-hydroxybenzotriazole in DMF/CH2Cl2. Benzylamine was reductively coupled to this bead-linker using sodium cyanoborohydride in 0.5M acetate buffer, pH 5, by the procedure in the same document. The product was then acetylated using acetic anhydride/triethylamine. The acetylated amine was released from the resin by treatment with 50% TFA/CH2Cl2 for 4 hours. The filtrate was evaporated to dryness and the residue evaluated by NMR and mass spectroscopy to show that the major product was N-benzylacetamide. This example demonstrates the feasibility of conducting solid phase synthesis using azlactone-functionalized beads.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US07820785B2 |
|---|
| 出典データセット | uspto-grants-2010_10 |
|---|
| ORD ID | ord-45d2d54a1e6843298127398bdf4de6a0 |
|---|
| 出典メモ | uspto-grants-2010_10 |
|---|
