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Methanol → 2'-O-{2-[(Dimethylamino)oxy]ethyl}-5-methyluridine
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Methanol | HCID 887 | — |
| 反応物 | Triethylamine | HCID 8471 | — |
| 反応物 | N,N-Diethylethanamine trihydrofluoride | HCID 175505 | — |
| 反応物 | 5'-O-tert-butyldiphenylsilyl-2'-O-[N,N-dimethylaminooxyethyl)-5-methyluridine | HCID 22947701 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | 2'-O-{2-[(Dimethylamino)oxy]ethyl}-5-methyluridine | HCID 22947699 | 92.5% |
反応手順
Triethylamine trihydrofluoride (3.91 mL, 24.0 mmol) was dissolved in dry THF and triethylamine (1.67 mL, 12 mmol, dry, kept over KOH). This mixture of triethylamine-2HF was then added to 5′-O-tert-butyldiphenylsilyl-2′-O-[N,N-dimethylaminooxyethyl]-5-methyluridine (1.40 g, 2.4 mmol) and stirred at room temperature for 24 hrs. Reaction was monitored by TLC (5% MeOH in CH2Cl2). Solvent was removed under vacuum and the residue placed on a flash column and eluted with 10% MeOH in CH2Cl2 to get 2′-O-(dimethylaminooxyethyl)-5-methyluridine (766 mg, 92.5%).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US06855700B2 |
| 出典データセット | uspto-grants-2005_02 |
| ORD ID | ord-17462780994649d1835da30b9c297b2d |
| 出典メモ | uspto-grants-2005_02 |