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Sodium Chloride → [(r)-2-(Tert-butyl-dimethylsilanyloxy)-1-(1-ethoxy-2-iodoethoxymethyl)-ethyl]-carbamic acid tert-butyl ester
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Sodium Chloride | HCID 5234 | — |
| 反応物 | Acetonitrile | HCID 6342 | — |
| 反応物 | Ethyl vinyl ether | HCID 8023 | — |
| 反応物 | N-Iodosuccinimide | HCID 120273 | — |
| 反応物 | (R)-(+)-N-(tert-Butoxycarbonyl)-O-(tert-butyldimethylsilyl)serinol | HCID 10913779 | — |
| 生成物 | [(r)-2-(Tert-butyl-dimethylsilanyloxy)-1-(1-ethoxy-2-iodoethoxymethyl)-ethyl]-carbamic acid tert-butyl ester | HCID 86615364 | 34% |
反応手順
Dissolve [(R)-1-(tert-butyl-dimethylsilanyloxymethyl)-2-hydroxyethyl]-carbamic acid tert-butyl ester (1.0 g, 3.27 mmol) and ethyl vinyl ether (0.20 g, 2.73 mmol) in acetonitrile (20 mL) and add N-iodosuccinimide (0.735 g, 3.27 mmol). Stir at room temperature 72 hours and pour into saturated aqueous sodium chloride. Extract with ethyl acetate, wash with water and saturated aqueous sodium chloride, dry (magnesium sulfate), filter and concentrate. Purify (silica gel chromatography, eluting with 100:0 to 10:90 hexanes:ethyl acetate) to give the desired compound (462 mg, 34%).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07745438B2 |
| 出典データセット | uspto-grants-2010_06 |
| ORD ID | ord-86666333ce9343dcba6d302be914e1c2 |
| 出典メモ | uspto-grants-2010_06 |